I am pleased to invite you to attend the 2024 Annual Meeting of Stockholders (the “Annual Meeting”) of Lands’ End, Inc. (the “Company” or “Lands’ End”) on Thursday, May 9, 2024. The meeting will begin at 9:00 a.m. (Central Time) at the Gary C. Comer Activity Center, 3 Lands’ End Lane, Dodgeville, Wisconsin 53595.

Whether or not you plan to attend the Annual Meeting in person, please read the Proxy Statement and vote your shares. Instructions for internet and telephone voting are included in your proxy card (if you received your materials by mail).

An admission ticket (or other acceptable proof of stock ownership) and a form of government-issued photo identification (such as a valid driver’s license or passport) will be required for admission to the Annual Meeting. Only stockholders who own Lands’ End common stock as of the close of business on March 20, 2024, will be entitled to attend the Annual Meeting. An admission ticket will serve as verification of your ownership.

If your Lands’ End shares are held in a bank or brokerage account, you can attend the annual meeting if you bring a recent bank or brokerage statement showing you owned shares of Lands’ End common stock on March 20, 2024. You may also contact your bank or broker to obtain a written legal proxy.

Registration will begin at 8:15 a.m. and seating will begin at 8:30 a.m. Use of cameras, recording devices, and other electronic devices will not be permitted at the Annual Meeting.

Please attend the 2024 Annual Meeting of Stockholders (the “Annual Meeting”) of Lands’ End, Inc. (the “Company,” “Lands’ End,” “our company,” “we,” or “our,”) to:

The record date for determining stockholders entitled to notice of, and to vote at, the Annual Meeting is March 20, 2024. Only stockholders of record at the close of business on that date can vote at, or will be eligible to attend, the Annual Meeting.

On or about April 10, 2024 we began mailing proxy materials to all stockholders of record as of March 20, 2024 and posted our proxy materials to www.proxyvote.com.

It is important that your shares are represented at the Annual Meeting. You may vote your shares

(1) in person at the Annual Meeting, (2) by telephone, (3) through the Internet, or (4) by completing and mailing a proxy card if you receive your proxy materials by mail. Specific instructions for voting by telephone or through the Internet (including voting deadlines) are included in the proxy card. If you attend and vote at the Annual Meeting, your vote at the Annual Meeting will replace any earlier vote.

The accompanying proxy is being solicited on behalf of the Lands’ End, Inc. (the “Company,” “Lands’ End,” “our company,” “we,” “our,” or “us”) Board of Directors (the “Board”) for use at the Annual Meeting of Stockholders to be held on May 9, 2024 (the “Annual Meeting”). On or about April 10, 2024, the Company began mailing to stockholders proxy materials, including instructions on how to access proxy materials via the Internet and how to vote online (www.proxyvote.com).

The Company’s Proxy Statement for the 2024 Annual Meeting of Stockholders and the Annual Report on Form 10-K for the fiscal year ended February 2, 2024 are available at www.proxyvote.com.

The Lands’ End Board of Directors is committed to effective corporate governance. The Board has approved and adopted Corporate Governance Guidelines that provide the framework for Lands’ End’s governance. The Nominating and Corporate Governance Committee of the Board reviews and assesses the Corporate Governance Guidelines annually and recommends changes to the Board as appropriate. The Corporate Governance Guidelines, along with the charters of Board committees, our Director Compensation Policy, our Code of Conduct and our Board of Directors Code of Conduct are available on our website at www.landsend.com, under the heading “Investor Relations” and then “Corporate Governance.”

Among other things, the Corporate Governance Guidelines provide that:

Based on the review and recommendation by the Nominating and Corporate Governance Committee, the Board analyzed the independence of each director. In making its independence determinations, the Board considers transactions, relationships and arrangements, if any, between Lands’ End and entities with which directors are associated as executive officers, directors and trustees. When these transactions, relationships and arrangements exist, they are in the ordinary course of business and are of a type customary for a company like Lands’ End.

As a result of this review, the Board affirmatively determined that the following director nominees meet the standards of independence under the applicable Nasdaq Stock Market listing rules, including that each member is free of any relationship that would interfere with their individual exercise of independent judgment:

The Board also has determined that each member of the Audit Committee meets additional, heightened independence criteria applicable to audit committee members under the Nasdaq Stock Market listing rules and SEC Rule 10A-3, and each of Robert Galvin, Josephine Linden, and John T. McClain is an “audit committee financial expert” as defined in Item 407(d)(5) of Regulation S-K promulgated by the SEC.

The Board also has determined that all members of the Compensation Committee and of the Nominating and Corporate Governance Committee meet independence criteria applicable to such committee members under the Nasdaq Stock Market listing rules.

Item 1 is the election of six nominees to our Board: Robert Galvin, Elizabeth Leykum, Josephine Linden, John T. McClain, Andrew J. McLean and Alicia Parker. Alicia Parker is being nominated for the first time, and each of the other nominees is a current member of the Board. If elected, each nominee will hold office until the next annual meeting or until their successor is elected and qualified, or earlier death, resignation, disqualification or removal. The Board currently has seven members: Robert Galvin, Elizabeth Leykum, Josephine Linden, John T. McClain, Andrew J. McLean, who are standing for reelection, as well as Jignesh Patel and Jonah Staw, who are not standing for reelection. By resolution of the Board in accordance with the Company’s Bylaws, effective upon the 2024 Annual Meeting, the size of the Board will be reduced to six members. We wish to thank Jignesh Patel and Jonah Staw, who have each served on the Board since 2014, for their many years of distinguished service on the Board and their dedication to the Company.

The persons named in the proxy card (the “proxies”) will vote FOR the election of all of the nominees listed below, unless otherwise instructed. You may not vote for a greater number of persons than the number of nominees named in this Proxy Statement. The Board expects all nominees to be available for election. If any nominee should become unavailable to serve as a director for any reason prior to the Annual Meeting, the Board may substitute another person as a nominee. In that case, your shares will be voted for that other person.

The biographies of each of the nominees and members of the Board below contains information regarding the person’s service as a director, business experience, education, public company director positions held currently or at any time during the last five years, information regarding involvement in certain legal or administrative proceedings, if applicable, and the experiences, qualifications, attributes or skills that caused the Board to determine that the person should serve as a director for the Company.

Alicia Parker, 47, has been nominated for election to the Board for the first time at the Annual Meeting. Since 2021 she has served as Chief Marketing Officer of Tishman Speyer, a leading international real estate owner, developer, operator and investment manager. Previously she served as Vice President, Brand & Consumer Marketing of Casper Sleep from 2020 to 2021, and as Director of Sales and Marketing of the Peninsula Hotels from 2017 to 2020. Prior to that she served as Senior Director, Marketing from 2013 to 2017, and Global Brand & Program Director from 2012 to 2013, for Ralph Lauren. She also served as Senior Vice President, Marketing and Business Strategy of Agenda from 2011 to 2012, and as Group Account Director of RDA from 2007 to 2011. She also worked in public relations from 2006 to 2007 at Warner Bros. Records and served as a Brand Marketing Consultant and Producer from 2004-2006. She served as Manager, Global Partner Network from 2001 to 2004, and Associate/Associate Manager from 1998 to 2000 for Strategic Management Group, Inc. Ms. Parker brings to the Board an extensive and dynamic understanding of marketing, brand development and sales, from both her in-house and agency experience in a variety of industries.

Robert Galvin, 64, joined the Board in May 2014. Since October 2018, he has served as President and Chief Executive Officer of Iconix International, formerly Iconix Brand Group, Inc., a leading brand management company, which Mr. Galvin also served as a member of the board of directors from October 2018 to August 2021. From January 2014 to October 2018, he was the principal of Galvin Consulting, which he founded in January 2014. Mr. Galvin served as the Chief Executive Officer of Elie Tahari, a leading global designer lifestyle brand, from January to November 2013. Prior to that, he served as the President of Camuto Group, a leading global women’s fashion footwear company from April 2007 to January 2012. Mr. Galvin previously served as the Chief Operating Officer of Sport Brands International, a global wholesale and retail athletic branded company from 2003 until April 2007. He previously held leadership roles at Kurt Salmon Associates, York International and Nine West Group Inc. Mr. Galvin served as a member of the board of directors of Big 5 Sporting Goods Corporation from July 2015 to October 2018, bebe stores, inc. from November 2014 to September 2018, Cherokee Inc. (now Apex Global Brands Inc.) from June 2012 to October 2018 and Trans World Entertainment Corporation from June 2018 to October 2018. Mr. Galvin has a B.S. in Accounting from

Fairfield University and a M.B.A. from New York University, Stern School of Business. Mr. Galvin brings an extensive knowledge of the apparel industry and management experience, gained through his service as Chief Executive Officer and through numerous senior executive positions at several apparel companies for more than 15 years.

Elizabeth Leykum, 45, joined the Board in March 2014. She has served as founder of Serenade Capital LLC, an investment firm, since May 2016. From October 2013 to April 2016, she served as a founding principal of HEG Capital LLC, a Connecticut-registered investment advisory firm. Prior to joining HEG Capital,

Josephine Linden, 72, joined the Board in March 2014 and has served as Chair of the Board since October 2014. She founded and has been the managing member and principal of Linden Global Strategies LLC, a New York-based SEC registered investment management firm working with sophisticated U.S. and international clients, since September 2011. From September 2010 to July 2011, she held an Adjunct Professor position in the Finance department of Columbia Business School. In November 2008, Mrs. Linden retired from Goldman, Sachs & Co. as a Partner and Managing Director after having been with the firm for more than 25 years, where she held a variety of roles, including Managing Director and Regional Manager of the New York office for Private Wealth Management, head of Global Equities Compliance, and an Advisor to GSJBWere, Australia. She currently serves on the Investment Committee of the Collegiate School in New York, New York, where she previously served as Treasurer and as a trustee, sat on the executive committee, and served as Chair of its Finance, Audit and Nominating Committees. She previously acted as Financial Advisor to The Prince of Wales Foundation. She previously served as a director of Sears Hometown and Outlet Stores, Inc. from October 2012 to October 2019 and as a director of Trine Acquisition Corp. from May 2019 to December 2020. Mrs. Linden has also served as a non-executive director of E&P Financial Group Limited (formerly Evans Dixon Limited) since May 2018, and as a director of Trine II Acquisition Corp. from November 2021 to April 2023. She received an M.B.A. from the University of Chicago, with a specialization in Finance, and a B.A. from the University of Sydney. In September 2022, Mrs. Linden was appointed an Honorary Member in the General Division of the Order of Australia for her significant service to the Australia-United States bilateral relationship, the international finance sector, and the professional development of Australia. Mrs. Linden brings extensive knowledge of capital markets and other financial matters to the Board from her 25-year career with Goldman Sachs.

John T. McClain, 63, joined the Board in May 2014. Since February 2019, he has served as Executive Vice President and Chief Financial Officer of Iconix International, formerly Iconix Brand Group, Inc., a leading brand management company. From November 2015 to September 2016, he served as Chief Financial Officer of Lindblad Expeditions Holdings, Inc., a global provider of expedition cruises and adventure travel experiences. Mr. McClain served as the Chief Financial Officer of The Jones Group Inc., a leading global designer, marketer and wholesaler of over 25 brands, from July 2007 until the sale of the company to Sycamore Partners in April 2014. From April 2014 to August 2014, he continued to provide Senior Advisor services related to financial operations to The Jones Group Inc. Prior to that, Mr. McClain held a number of roles at Avis Budget Group, Inc., formerly Cendant Corporation. He joined Cendant Corporation in September 1999, serving as the Senior Vice President, Finance & Corporate Controller until 2006. From 2006 to 2007, Mr. McClain served as the Chief Accounting Officer of Avis and Chief Operating Officer of Cendant Finance Holdings. Mr. McClain previously held leadership roles at Sirius Satellite Radio Inc. and ITT Corporation. Mr. McClain has served as a trustee of Seritage Growth Properties, a real estate investment trust, since June 2015. He previously served on the board of Nine West Holdings from April 2014 until October 2015, and on the board of Cherokee Inc. (now Apex Global Brands Inc.) from September 2017 to January 2019. Mr. McClain holds a B.S degree in accounting from Lehigh University. Mr. McClain brings over 25 years of executive financial experience, serving at high-level capacities for the retail and consumer sectors.

Andrew J. McLean, 55, has served as the Chief Executive Officer since January 2023. He joined Lands’ End as Chief Executive Officer-Designate and member of the Board of Directors in November 2022. Prior to joining the Company, he served at American Eagle Outfitters, Inc., the parent of the American Eagle and Aerie brands, from October 2016 to September 2022, in the roles of President, International from August 2022 to September 2022, Executive Vice President, Chief Commercial Officer from April 2017 to August 2022, and Executive Vice President, International from October 2016 to April 2017. Mr. McLean served Urban Outfitters, Inc. as Chief Operating Officer and Head of International from 2014 to October 2016, and as Chief Operating Officer from 2008 to 2014. Mr. McLean held various positions at Liz Claiborne, Inc., including President, Outlet Division, from 2003 to 2008, as well as, various positions at Gap, Inc. from 2000 to 2003. Mr. McLean began his career as a strategy consultant with AT Kearney. Outside of his professional commitments, Mr. McLean is an active member of the Duke University parents committee, where he acts as a parent ambassador and student mentor. Mr. McLean received his Bachelor’s degree in Engineering from the University of Manchester, a Master’s degree in Engineering Management from the University of Cambridge and an MBA from Harvard Business School. Mr. McLean brings to the Board extensive operational and strategic expertise and over 20 years of retail experience leading organizational growth for several Fortune 500 and start-up companies. Mr. McLean has a proven track record in the areas of global brand delivery and international strategy, marketing and customer experience.

The Nominating and Corporate Governance Committee of our Board is responsible for reviewing the qualifications and independence of members of the Board and its various committees on a periodic basis, as well as the composition of the Board as a whole. This assessment includes members’ qualification as independent, as well as consideration of skills and experience in relation to the needs of the Board. New director nominees are recommended to the Board by the Nominating and Corporate Governance Committee. The ultimate responsibility for selection of director nominees resides with the Board.

The Board believes that diversity promotes innovation and is integral to honoring Lands’ End’s commitment to “Take care of the customer, take care of the employee and the rest will take care of itself.” We are deeply committed to hiring and promoting inclusively, championing pay equity, increasing diverse representation at all levels of Lands’ End, and fostering an inclusive culture where our employees can develop and grow professionally, and contribute to our collective success. We believe the Board exhibits the diversity we foster within our employees.

While the Company does not have a formal Board diversity policy, the Board considers diversity, including diversity of racial, ethnic, gender and socio-economic background, in identifying director nominees. The Board and the Nominating and Governance Committee believe that it is important that our directors represent diverse viewpoints. In addition to diversity of experience, the Nominating and Corporate Governance Committee seeks director candidates with a broad diversity of professions, skills and backgrounds. The Nominating and Corporate Governance Committee discusses Board composition, including the diversity of the Board, annually. Of the current seven members of the Board, two directors are female and one director is of South Asian descent and, of our six nominees, three are female. The table below sets forth diversity information regarding our Board of Directors:

The Nominating and Corporate Governance Committee of the Board of Directors oversees Environmental, Social and Governance (ESG) through reviewing with management the Company’s ESG strategies, initiatives and policies. In addition, the Board and its committees review and discuss with management matters related to human capital management, including Lands’ End’s commitments and progress on inclusion and diversity, employee engagement, compensation and benefits, business conduct and compliance, and executive succession planning.

The Board believes that good stewardship of the environment is fundamental to Lands’ End’s long-term success, and Lands’ End is working towards improving its sustainable footprint through key practices like waste reduction, purchasing recycled consumables and through corporate relationships. Lands’ End hopes to inspire customers and other corporations to increase sustainability awareness and initiatives.

We have a focus on raising awareness and educating employees on reducing our internal use of consumables and natural resources. In addition, we have a broad range of recycling and waste management initiatives at our

corporate office and distribution centers. For example, we have implemented practices to reduce our use of office paper products and plastics, recycle aluminum cans and glass and work with partners to reuse electronic equipment before recycling, as well as disposal of non-recyclables with an on-campus composting site. We also focus on efficient water and energy management programs. Additional information and periodic updates regarding our sustainability policies and procedures can be found on our website at https://www.landsend.com/ sustainability/.

We have set in place and published the following sustainability priorities and goals regarding our products:

Lands’ End and its subsidiaries and affiliates are committed to having a positive role in promoting the sustainability of forests and other natural resources. Our objective is to encourage a sustainable combination of resources and processes to produce the paper for catalogs, internal use, and direct mail.

Lands’ End also participates in industry educational workshops and initiatives. We have formed strategic relationships with organizations like the Sustainable Apparel Coalition, National Forest Foundation, through which we have funded the planting of nearly 1.4 million trees, and the Clean Lakes Alliance, where we help protect and improve maintenance of local lakes in Wisconsin. These alliances, which respectively operate globally, nationally, and locally, allow us to engage at a variety of levels.

Since our founding in 1963, Lands’ End has recognized that our people are a critical asset. People, the individuals we employ, the customers we serve, and their families, are the heart of our company. We are committed to creating an inspiring culture that is welcoming, safe and inclusive for all who work and shop with us. Our founder, Gary Comer set the foundation with this quote: “The really important thing that makes Lands’ End what it has become is people. You, me, everyone around us. It is what we do as people that makes this a great place to come to work.”

We employ approximately 4,900 employees: approximately 4,400 employees in the United States and approximately 500 employees outside the United States. The U.S. workforce consists of approximately 50% part-time employees, 32% hourly employees and 18% salaried employees. With the seasonal nature of the fourth quarter holiday shopping season in the retail industry, approximately 1,500 additional, flexible, part-time employees are hired in the U.S. to support our customer service and distribution centers.

For an additional discussion about Human Capital, please see Part I, Item 1. Business “Human Capital Management” in our Annual Report on Form 10-K for the fiscal year ended February 2, 2024.

Lands’ End is committed to conducting business with a high standard of business ethics, a regard for human rights and in compliance with all applicable laws. Moreover, Lands’ End expects its product vendors to maintain similar standards in its entire supply chain, including but not limited to raw materials, fabric and trim suppliers, employee recruitment services as well as any secondary processing facilities whether owned, leased or contracted. Lands’ End maintains a robust compliance program and holds its vendors to high ethical standards. Lands’ End has a long-standing Code of Conduct for its supply chain partners which prohibits the use of forced labor, modern slavery or human trafficking within our supply chain anywhere in the world. Lands’ End, in response to crisis in the Xinjiang Uyghur Autonomous Region, removed suppliers who could not demonstrate compliance with its policies, and requires that for any fabric produced in China all cotton used be 100% sourced outside of China from certified sources. Additionally, Lands’ End has shifted a sizeable amount of its production from China to other regions, such as Southeast Asia and the Indian sub-continent. The Global Compliance Program Requirements and the related processes, policies and procedures set forth certain basic and fundamental requirements that all domestic and international vendors must satisfy as a condition of doing business with Lands’ End. The requirements are developed based on local and national laws, International Labour Organization (ILO) conventions and benchmarked against industry protocols. Lands’ End utilizes an independent auditor to conduct factory inspections to ensure compliance with its Code of Conduct and its Global Compliance Program. Lands’ End maintains an Ethics Hotline for reporting of suspected violations of its Code of Conduct and its policies by vendors, employees or customers. It also requires posters to be placed in all factories with reporting information for suspected violations.

The Board met 6 times during fiscal year 2023. All of the directors attended over 75% of the total number of meetings of the Board and meetings of the committees on which they served. Our Corporate Governance Guidelines provide that directors are expected to attend the Annual Meetings of Stockholders, and typically all directors are in attendance.

The Board has standing Audit, Compensation, and Nominating and Corporate Governance committees. The table below reflects the current membership of each committee and the number of meetings held by each committee during fiscal year 2023.

Each committee operates under a written charter. The charters are available at the “Corporate Governance” page in the “Investor Relations” section of www.landsend.com under the heading “Corporate Governance Documents.” The principal functions of each Committee are summarized below.

Our Board has adopted a policy and process for stockholders to communicate with the Board or an individual director. Stockholders may communicate with the Board collectively, or with any of its individual non-employee directors, by writing to Lands’ End, Inc. Board of Directors, c/o Secretary, Lands’ End, Inc., Legal Department, 1 Lands’ End Lane, Dodgeville, Wisconsin 53595. The Secretary has discretion to determine whether stockholder communications are proper for submission to the intended recipient. Examples of stockholder communications that would be considered presumptively inappropriate for submission include the following: communications regarding personal solicitations; spam and other junk mail; new product suggestions; resumes and other job inquiries; business solicitations or advertisements; communications that are unduly hostile, threatening, illegal, or similarly unsuitable; and communications that are frivolous in nature.

We currently separate the roles of Chief Executive Officer and Chair of the Board. Our Chief Executive Officer is responsible for the day-to-day leadership and performance of the Company, while the Chair of the Board provides guidance to our Chief Executive Officer and senior management and sets the agenda for and presides over our Board meetings. In carrying out her responsibilities, the Chair preserves the distinction between management and oversight, maintaining the responsibility of management to develop corporate strategy and the responsibility of the Board to review and express its views on corporate strategy and management’s execution of that strategy.

Consistent with our leadership structure, our Chief Executive Officer and other members of senior management are responsible for the identification, assessment, and management of risks that could affect the Company and the Board provides oversight in connection with these efforts. We do not believe that the Board’s role in risk oversight has an effect on the Company’s leadership structure. The Board’s oversight is conducted primarily through committees of the Board, as disclosed in the descriptions of the responsibilities of the Audit Committee and the Compensation Committee above and in the charters of such committees.

The Audit Committee is responsible for oversight of (1) risks and exposures associated with financial matters, particularly financial reporting, tax, accounting, disclosure, internal control over financial reporting, and credit and liquidity matters; (2) the Company’s enterprise risk management framework, including data protection and cybersecurity risk; and (3) the steps management has taken to monitor and control risks and exposures, including the Company’s risk assessment and risk management policies and strategies and programs and policies relating to legal compliance.

The Compensation Committee evaluates whether the risks arising from the Company’s compensation policies and practices for its employees would be reasonably likely to have a material adverse effect on the Company and has received management’s determination that our programs do not create risk that is reasonably likely to have a material adverse effect on the Company.

The Board has retained responsibility for general oversight of risks. The Board satisfies this responsibility through full reports by each committee chair regarding the committee’s considerations and actions, as well as through regular reports directly from officers responsible for oversight of particular risks within the Company, including our Chief Financial Officer, our General Counsel, our Chief Technology Officer and our most senior internal audit and information security professionals.

Directors may be nominated by the Board or by stockholders in accordance with our Bylaws. The Nominating and Corporate Governance Committee will, when it deems appropriate, actively seek individuals qualified to become Board members, and will solicit input on director candidates from a variety of sources, including current directors. The Committee will evaluate a candidate’s qualifications and review all proposed nominees for the Board, including those proposed by stockholders, in accordance with its charter and our Corporate Governance Guidelines. This will include a review of the person’s qualifications and independence as well as consideration of diversity, age, skills, education and experience in the context of the needs of the Board. The Committee has the ability to retain a third party to assist in the nomination process.

Director nominees recommended by the Nominating and Corporate Governance Committee are expected to be committed to representing the long-term interests of our stockholders. The Committee believes that it is important to align the interests of directors with those of our stockholders. Generally, each non-employee director is required to acquire a number of shares of our common stock in an amount that, at cost, is equal to the amount of the director’s annual retainer in effect on the date when the director first becomes a member of the Board. Non-employee directors must meet this requirement by the third anniversary of that date unless, due to employment or legal restrictions, he or she is unable to acquire our common stock. As of February 2, 2024, all non-employee directors were in compliance with this requirement. Board members should possess a high degree of integrity and have broad knowledge, experience and mature judgment. In addition to a meaningful economic commitment to our company as expressed in share ownership, directors and nominees should have predominately business backgrounds, have experience at policy-making levels in business and/or technology, and bring a diverse set of business and life experiences and perspectives to the Board.

Mr. McLean’s employment letter with the Company provides for his appointment to the Board and provides that while he is Chief Executive Officer, he will be nominated for reelection to the Board each time his term as director is scheduled to expire. In addition, under his executive severance agreement with the Company, a termination of employment by Mr. McLean is for “Good Reason” if, among other events, at any time that ESL Investments, Inc. and its affiliate entities beneficially own more than 20% of the Company’s shares entitled to vote for directors, they, in whole or in part, vote against his reelection to the Board while Mr. McLean is serving as the Company’s Chief Executive Officer.

A Lands’ End stockholder can nominate a candidate for election to the Board by complying with the nomination procedures in our Bylaws, which provide that for an election to be held at an annual meeting of stockholders, nomination by a stockholder must be made by notice in writing delivered to the Company not later than the 90^th day, and not earlier than the 120^th day, prior to the first anniversary of the preceding year’s annual meeting. If the date of the subject annual meeting is more than 30 days before or more than 70 days after the first anniversary of the preceding year’s annual meeting, notice by the stockholder must be delivered not earlier than the 120^th day prior to the annual meeting and not later than the later of the 90^th day prior to the annual meeting or the 10^th day following the day on which public announcement of the date of such annual meeting is first made by the Company. For an election to be held at a special meeting of stockholders, the stockholder’s notice in writing must be delivered to the Company not earlier than the 120^th day prior to the special meeting and not later than the later of the 90^th day prior to the special meeting or the 10^th day following the day on which public announcement is first made of the date of the special meeting and of the nominees proposed by the Board to be elected at the special meeting.

A stockholder’s written notice to the Secretary described in the preceding paragraph must be delivered to Lands’ End, Inc., Attn: Secretary, 1 Lands’ End Lane, Dodgeville, Wisconsin 53595. Any stockholder of record or beneficial owner of common stock proposing such a nomination must be a stockholder of record on the date of the giving of such notice and on the record date for the determination of stockholders entitled to notice of and to vote at the meeting of stockholders and comply with the applicable notice procedures set forth in the Company’s Bylaws, including setting forth the following in the written notice: (i) the name and address of the stockholder; (ii) the number of shares of capital stock of the Company owned beneficially and of record by the stockholder; (iii) a description of any agreement, arrangement or understanding with respect to the nomination between or among the stockholder, any of its affiliates or associates, each nominee and any others acting in concert with any of the foregoing; (iv) a description of any agreement, arrangement or understanding that has been entered into as of the date of the stockholder’s notice by, or on behalf of, the stockholder, the effect or intent of which is to mitigate loss to, manage risk or benefit of share price changes for, or increase or decrease the voting power of, the stockholder with respect to securities of the Company; (v) a representation that the stockholder is a holder of record of stock of the Company entitled to vote at the meeting and intends to appear in person or by proxy at the meeting to propose each nomination; (vi) a representation whether the stockholder intends or is part of a group that intends (a) to deliver a proxy statement and/or form of proxy to holders of at least the percentage of the Company’s outstanding capital stock required to elect each nominee and/or (b) otherwise to solicit proxies or votes from stockholders in support of each nomination; (vii) the name, age and business address of each nominee proposed in the notice; (viii) all information concerning the stockholder and each nominee required to be disclosed in proxy solicitations for director elections under the proxy rules of the SEC; and (ix) the written consent of each nominee to serve as a director if so elected.

The Company may require any proposed nominee to furnish such other information as the Company may reasonably require to determine the eligibility of the nominee to serve as a director. The chair of any annual meeting or special meeting of stockholders may refuse to acknowledge the nomination of any person not made in compliance with the foregoing procedures. In addition to satisfying the foregoing requirements under the Company’s Bylaws, to comply with the universal proxy rules, stockholders who intend to solicit proxies in support of director nominees other than Lands’ End’s nominees must provide notice that sets forth the information required by Rule 14a-19 under the Exchange Act no later than March 10, 2025. Any decision to include information regarding a proposed nominee in the Company’s proxy solicitation materials will be made in accordance with the Company’s Bylaws and applicable law.

Our Director Compensation Policy provides for an annual cash retainer for serving as a non-employee director of the Company, for serving as Board Chair, and for serving as the chair or member of committees as follows:

In addition, the Director Compensation Policy provides that our non-employee directors may elect annually to receive all or a portion of their retainer in the form of shares of Lands’ End common stock. Non-employee directors also receive an annual Lands’ End gift card in the amount of $10,000, as well as a discount on the purchase of Lands’ End merchandise under a program available to all Lands’ End employees. Upon the approval on a case-by-case basis of the Nominating and Corporate Governance Committee, a non-employee director may participate in health care programs of the Company on a basis no less favorable than senior executives of the Company. The Nominating and Corporate Governance Committee conducts regular reviews of Board compensation, and considers publicly available board compensation data and best market practices.

The following table shows information concerning the compensation earned in fiscal year 2023 by directors who served on the Board during fiscal year 2023 and are not named executive officers.^*

The following table sets forth certain information regarding beneficial ownership of our common stock as of March 28, 2024 for (1) each person known to us to be the beneficial owner of more than 5% of our common stock; (2) each named executive officer; (3) each of our current directors and nominees; and (4) all of our executive officers and directors as a group.

The Company has adopted an Insider Trading Policy, designed to promote compliance with insider trading laws, rules and regulations, as well as applicable exchange listing standards. The policy is applicable to the Company’s officers, employees, members of the Board of Directors and other designated persons with access to Company material nonpublic information, as well as to family members residing with them and any entities or family members whose transactions in the Company’s securities are directed by or subject to their influence and control. The Insider Trading Policy prohibits the trading of Company securities on the basis of material, nonpublic information and establishes regular blackout periods wherein certain designated persons are prohibited from trading in Company securities. It also prohibits engaging in, among other things, short sale transactions and hedging transactions with respect to Company securities, including through the use of financial instruments such as prepaid variable forwards, equity swaps, collars and private exchange funds, and prohibits holding Company securities in a margin account or otherwise pledging Company securities as collateral for a loan.

This Compensation Discussion and Analysis provides information to assist you in understanding the fiscal year 2023 compensation of the executive officers identified in the Summary Compensation Table, whom we refer to as our “named executive officers.” Our named executive officers for fiscal year 2023 are:

During fiscal year 2023, Mr. McCracken served as Interim Chief Financial Officer until September 2023, when he was appointed Chief Financial Officer. In June 2023, Ms. Rieger became an executive officer due to changes in responsibilities. Ms. Rasmusen’s employment ceased in connection with a position elimination on September 5, 2023.

Fiscal year 2023 was a year of transition for Lands’ End. As planned, Andrew McLean succeeded Jerome Griffith as Chief Executive Officer at the conclusion of fiscal year 2022. In contrast to fiscal year 2022, where macroeconomic factors had a profound impact on our business, during fiscal year 2023 inflationary pressures subsided, freight costs normalized, and costs of raw materials, packaging materials, labor, transportation, energy, fuel and other inputs necessary for the production and distribution of our products, stabilized. In addition, over the course of the year, we focused on shifting the business toward higher margin selling, addressing inventory management challenges from fiscal year 2022, introducing and emphasizing newness into our product offering, shifting our customer focus from demographics to behaviors in order to better attract and retain our key customer cohorts and refinancing our term loan. In these areas, we made sizable progress, which resulted in Adjusted EBITDA of $84.3 million, an approximately 20% increase over fiscal year 2022.

Based on our performance relative to pre-established adjusted EBITDA goals, our annual incentive plan for fiscal year 2023 paid out at 78% of target. However, our long-term performance-based awards for the fiscal 2021 through 2023 period yielded no payout and those awards expired without vesting.

Our return to office efforts continued over the course of fiscal year 2023. Building on our “collaboration weeks” where, beginning in fiscal year 2022 many employees were encouraged to work from our corporate offices one designated week per month, we have further expanded our return to office efforts, with our senior management (Vice President and above) and most other corporate staff, working in person three weeks every month. We believe this transition back to office has reinforced our commitment to culture, collaboration and innovation.

The Compensation Committee believes that our long-term success is directly related to our ability to attract, motivate and retain highly talented executives who are committed to our mission, results and cultural beliefs. The Compensation Committee has developed a compensation philosophy for our senior executives designed to

pay-for-performance. Accordingly, the total compensation packages provided to our named executive officers generally include both annual and long-term incentive opportunities that are linked to performance measures or are otherwise “at risk” due to market fluctuations and potential for forfeiture. For fiscal year 2023, approximately 78% of our CEO’s target compensation was considered at-risk, and approximately 63% of our other named executive officers’ target compensation was considered at-risk based on financial and relative total stockholder return (TSR) performance measures or the possibility of forfeiture.

Our compensation packages are designed in large measure to motivate and encourage executives to drive performance and achieve superior results for the Company and its stockholders. They also reflect other important considerations, such as the value of the position in the marketplace, levels of job responsibility, individual performance and the need to attract and retain top executive talent. The Compensation Committee grants equity-based incentives to align management’s and stockholders’ interests. While the Compensation Committee seeks to utilize compensation and benefit arrangements that reflect the pay-for-performance compensation philosophy, it recognizes that from time to time it may be appropriate for the Company to provide additional inducements, such as sign-on awards, spot bonuses and other provisions, to recruit, retain, reward and motivate highly qualified executives. Compensation agreements are discussed in “Employment Arrangements” below. No such additional inducements were utilized for any of the named executive officers in fiscal year 2023.

The key elements of our compensation program for our executives include base salary, annual cash incentive opportunities, long-term performance-based incentive opportunities and long-term time-based equity awards.

There is no pre-established policy or target for the allocation between annual and long-term incentive compensation. Instead, the Compensation Committee takes a holistic approach to executive compensation and the balance of the compensation elements for each executive individually. For fiscal year 2023, approximately 44% of our CEO’s target compensation and approximately 65% of our other named executive officers’ target compensation was annual in nature, while approximately 56% of our CEO’s target compensation and approximately 35% of our other named executive officers’ target compensation was long-term in nature. Additionally, approximately half of our CEO and other named executive officers’ long-term compensation was delivered in performance-based awards.

The Compensation Committee believes that a fair and effective way to motivate executives to produce superior results for stockholders is to increase the proportion of an executive’s total compensation that is performance-based or otherwise “at risk”, including equity compensation, relative to the executive’s ability to influence those results. Additionally, the Compensation Committee believes that the value of incentive compensation should depend upon the performance of the Company in a specified performance or vesting period. Under our incentive compensation structure, the highest amount of compensation can be achieved through consistent superior performance over successive periods. This approach is designed to provide incentives for managing long-term growth, while minimizing short-term excessive risk-taking.

During fiscal year 2023, the Compensation Committee sought to achieve the objectives of our compensation program for our named executive officers through the grant of annual and long-term incentive awards. The fiscal year 2023 annual incentive awards for the named executive officers offered an opportunity to earn cash compensation based upon achievement of annual and quarterly adjusted EBITDA (earnings before interest, taxes, depreciation and amortization) goals for fiscal year 2023. The goal-setting process is discussed below in “Fiscal Year 2023 Annual Incentive Opportunity”. In fiscal year 2023, the Compensation Committee also granted long-term time-based equity awards that will vest over a three-year period, assuming continued service and long-term performance-based equity awards, which vest based on achievement of cumulative adjusted EBITDA and revenue goals for a three-year period, and are subject to a relative total stockholder return (“Relative TSR”) modifier which is based on the Company’s total return to stockholders over the measurement period relative to a custom peer group. We use adjusted EBITDA in both our annual and long-term incentive program as we believe it is a key driver of long-term, sustained stockholder value.

Our target Annual Incentive Plan (As Amended and Restated) (“AIP”) awards and our long-term incentives are established based on a percentage of base salary. As the participating executive’s base salary is determined, in part, on their past performance, an award opportunity that is based on a multiple of that base salary also reflects, in part, their past performance.

Following the end of a performance period, the Compensation Committee certifies the level of achievement against the applicable financial performance goals established under the annual and long-term performance-based incentive programs, but retains the ability to exercise positive or negative discretion to adjust payout in relation to our annual and long-term performance. The Compensation Committee did not exercise any such discretion for fiscal year 2023 payouts for any of the named executive officers.

Base salaries are established at levels that generally reflect the past performance, experience, expected future contributions and responsibilities of the executive officer. The importance of the executive officer’s position, external pay data, market competitiveness and internal pay equity also are considered, as well as the extent of any promotions or other change in the executive’s responsibilities.

The following table sets forth the base salary as of fiscal year end 2023 for each of the named executive officers, and their prior year fiscal year end base salary:

The named executive officers’ base salaries were each set based on a combination of factors considered by Mr. McLean in recommending the base salaries of the named executives (other than Mr. McLean, whose base salary was determined solely by the Compensation Committee), and by the Compensation Committee in approving all of the base salaries (including Mr. McLean’s), including an assessment of individual achievements, contributions to the performance of the Company, changes in responsibilities, and peer group, general industry and survey comparisons. Mr. McCracken’s salary increased to $323,585 on May 20, 2023, and in addition to his base salary, from January 28, 2023 through September 13, 2023, Mr. McCracken also received an additional $15,000 per month for serving as Interim Chief Financial Officer. Mr. McCracken's salary was increased to $525,000 in connection with his appointment as Chief Financial Officer on September 14, 2023. Ms. Rieger’s base salary was increased to $500,000 effective January 22, 2024, in recognition of certain increased responsibilities.

As we rely upon “at risk” compensation to motivate our executives, in addition to time-based equity awards, in 2023 we utilized two forms of performance-based awards: awards based on goals set for fiscal year 2023 under the AIP (“2023 AIP”) and performance-based equity awards.

Under the 2023 AIP, we used, as in past years, an adjusted EBITDA measure (see discussion of this measure, and how it differs from reported Adjusted EBITDA below, in “Fiscal Year 2023 Annual Incentive Opportunity”). The adjusted EBITDA targets were established in April 2023. When establishing the performance goals for the 2023 AIP and also for the long-term performance-based equity awards granted in 2023, the Compensation Committee considered such factors as fiscal year 2022 financial results, overall fiscal year 2023 financial goals, our long-range plan, our competitive position, and market trends, as well as the general state of the economy and our business.

With respect to the long-term performance-based equity awards, performance goals are based on adjusted EBITDA and revenue goals, which considered the factors cited above, and were established in April 2023 for the cumulative three-year period from fiscal year 2023 through fiscal year 2025.

For the 2023 AIP, the Compensation Committee approved an adjusted EBITDA performance measure (“2023 AIP EBITDA”) that consisted of quarterly and annual goals, which cumulatively accounted for 100% of

the annual incentive opportunity for our named executive officers. The 2023 AIP EBITDA measure differs from “Adjusted EBITDA” which is a key metric reported by the Company. Adjusted EBITDA is used by management to measure business performance, in an effort to encourage growth and create increased stockholder value through the efficient use of corporate assets. For purposes of the 2023 AIP, reported Adjusted EBITDA results are subject to further adjustment as detailed below (see Item 7 Management’s Discussion and Analysis of Financial Condition And Results of Operations of our Annual Report on Form 10-K for a reconciliation of Net Income to Adjusted EBITDA).

Given the challenging business conditions present at the end of fiscal year 2022 and the beginning of fiscal year 2023, and in light of the Company’s financial performance in fiscal year 2022, the Compensation Committee deemed it critical that the opportunity to earn incentive compensation under the 2023 AIP be balanced with the need of the Company to maintain compliance with its debt covenants. Accordingly, in adopting the 2023 AIP, the Compensation Committee provided that no bonus amounts could be earned if such bonus amounts would cause the Company to fail to comply with the financial covenants included in its term loan. Since debt covenant compliance was to be measured quarterly, the 2023 AIP contained quarterly, as well as, annual goals. In addition, to incent management to deliver comparatively stronger results in fiscal year 2023, the metrics provided for both a “target” level of performance, which equated to 75% payout, and a “stretch target” level of performance, which would need to be attained to earn a 100% payout.

To determine 2023 AIP EBITDA performance, we first calculate Adjusted EBITDA, computed as operating income (loss) appearing on our statement of operations for the applicable reporting period, adjusted for depreciation, amortization, gains/(losses) on sales of assets and other items we determine affect the comparability of financial results from period to period. Then, in determining financial goal achievement relative to the 2023 AIP EBITDA measure, the Compensation Committee is required to adjust either the performance target or actual Adjusted EBITDA results to reflect the following occurrences affecting our results during the performance period:

Opportunities under the AIP for the participating executives are generally established upon hire and reviewed when the Compensation Committee reviews annual compensation or at the time a compensation package for a participating executive is otherwise approved, and reflects the participating executive’s relative level of responsibility and potential to affect our overall performance. The target award opportunity under the 2023 AIP was consistent with past practice and was set at 100% of base salary for Mr. McLean, and 75% of base salary for the other named executive officers. Mr. McCracken’s target award opportunity was initially set at 40% and increased to 75% due to his appointment as Chief Financial Officer. Threshold, target, stretch target and maximum levels for quarterly and annual performance under the 2023 AIP EBITDA were established in April 2023.

For the annual measure, as discussed above, performance levels were set at: threshold for performance at 12.5% below target 2023 AIP EBITDA for fiscal year 2023, target at our internal plan, which had been

established in April 2023 and represented a 13.5% increase over fiscal year 2022 performance, stretch target, which represented performance at 25% over fiscal year 2022 performance, and maximum at an approximately 25% overachievement of the stretch target for fiscal year 2023. For the quarterly measures, the performance levels per quarter were set equal to 25% of their annual counterparts, threshold each quarter was 12.5% below the target, the stretch target was set at an approximately 10% overachievement of the target, and maximum at an approximately 25% overachievement of stretch target. The annual incentive, which provided 100% payout for achievement of the stretch targets, equally weighted the achievement of quarterly goals and the annual goal, with 50% of the incentive opportunity based on each. The following table summarizes the plan design, metric, and performance levels:

The Compensation Committee views Adjusted EBITDA growth as a key metric and driver of stockholder value. As designed, each of the four fiscal quarters and the full fiscal year was measured independently and the 2023 AIP payout for each period depended upon at least threshold performance. If threshold performance was not achieved for a particular period, no payout would be made under the 2023 AIP for that period.

At the time it set the targets, the Compensation Committee believed that performance at the target level, a 13.5% improvement over fiscal year 2022 performance, was attainable, yet challenging, given multiple factors, including uncertainty related to supply chain challenges, and that performance at the stretch target level required for a 100% payout would be even more challenging to achieve.

Our quarterly and annual actual 2023 AIP EBITDA, and the resultant payout, was as follows:

These results yielded a payout of 78% of target for the named executive officers and other AIP participants. Neither the Compensation Committee nor the Board exercised any discretion with respect to the payout amounts, which are set forth below.

For fiscal year 2023, our long-term incentive (“LTI”) structure had two components: awards of performance-based restricted stock units (each, a “PRSU” and the award, the “2023 PRSU Awards”) and awards of time-based restricted stock units (each, an “RSU” and the award, the “2023 RSU Awards”) under the Lands’ End, Inc. Amended and Restated 2017 Stock Plan (the “2017 Stock Plan”), each weighted equally at 50% of the total LTI value.

Each of the named executive officers has a target incentive. For Mr. McLean the target incentive is $2,520,000 and for Mr. Gray, Ms. Rieger and Ms. Rasmusen the target incentive was set at 110% of base salary. At the time the LTI grants were made, Mr. McCracken’s target incentive was set at 50% of base salary. Beginning with fiscal year 2024 awards, Mr. McCracken’s target incentive is expected to be set at 110% of base salary.

The 2023 PRSU Awards are intended to focus the named executive officers on our long-term performance and align their interests with those of our stockholders. Each PRSU represents a contingent right to receive one share of our common stock upon satisfaction of adjusted EBITDA (75% weighting) (“2023 PRSU EBITDA”) and revenue (25% weighting) vesting conditions for the cumulative period comprised of fiscal years 2023 through 2025, and are subject to the Relative TSR modifier which is based on the Company’s total return to stockholders over a measurement period relative to a custom peer group and continued service. The 2023 PRSU Awards will vest, if at all, when the Compensation Committee determines whether a requisite level of performance has been achieved. The determination will take place after the conclusion of the third year of the performance period. Each named executive officer may earn a number of PRSUs and be issued the related number of shares, based on the Company’s performance relative to the cumulative adjusted EBITDA and revenue goals, and the Relative TSR modifier. All goals were set in April 2023.

The number of shares for the 2023 PRSU Awards at target level of performance to each of the named executive officers, representing 50% of their LTI value on June 14, 2023 (calculated using a value per share of $8.54, the closing price of the Common Stock on the date of the award), and the grant date fair value of the award (calculated using a value per share of $9.74, the award date closing price as adjusted to reflect the estimated value of the Relative TSR modifier; value adjustment calculated using a Monte Carlo simulation, described in Note 5. Stock-Based Compensation in our Annual Report on Form 10-K for the fiscal year ended February 2, 2024), are each set forth on the table below:

The definition of 2023 PRSU EBITDA is substantially the same as the definition of 2023 AIP EBITDA (as indicated above). Revenue for the purposes of the 2023 PRSU Awards, is revenue, as determined by GAAP. Under the 2023 PRSU Awards, a threshold level of performance for a goal will generate a preliminary payout calculation of 50% of 2023 Target Shares, a target level of performance will generate a preliminary payout calculation of 100% of 2023 Target Shares and a maximum level of performance will result in a preliminary payout calculation of 200% of 2023 Target Shares. The preliminary payout percentage calculation between each of threshold and target payout and between target and maximum payout is based on straight-line (linear) interpolations. Each metric is considered independently, and payout for that metric will be weighted according to the weighting associated with the metric. Once the preliminary payout percentage is determined, such amount is

subject to adjustment by applying the Relative TSR Modifier. The Relative TSR Modifier reflects a filtered subset of the combined S&P TMI Consumer Discretionary and Completion Consumer Discretionary indices based on the following criteria:

The foregoing approach yielded a comparator group of 38 companies. Application of the Relative TSR Modifier may not result in a payout in excess of 200% of target, and the Relative TSR Modifier is capped at 100% if our absolute TSR during the Relative TSR measurement period of April 1, 2023 through January 31, 2026 is negative.

A summary of the plan design for the 2023 PRSU Awards is set forth below:

Since the levels of achievement for the metrics are based on a three-year cumulative amount, fiscal year 2023 performance, alone, did not trigger any achievement.

All grants under the 2017 Stock Plan, including the 2023 PRSUs and any other grants to an individual in the same fiscal year, are subject to the limitations of the 2017 Stock Plan, including Section 7.1(b) which imposes a per participant limit.

The 2023 RSU Awards are intended to focus the named executive officers on our long-term performance, promote retention and align their interests with those of our stockholders. Each RSU represents a contingent right to receive one share of our common stock upon satisfaction of the vesting conditions. The 2023 RSU Awards will vest, subject to satisfaction of vesting conditions, including continued service, on the first, second and third anniversaries of the award date (with respect to 25%, 25% and 50% of the 2023 RSU Awards), which was June 14, 2023.

The number of shares for awards was determined by dividing the desired value (in case of the 2023 RSU Awards, 50% of the executive’s LTI value) by the closing price of our common stock on the date of grant. The closing price of our common stock on the award date was $8.54. Accordingly, the number of shares for the 2023 RSU Awards made to each of the named executive officers, and the grant date fair value of the award (based on such closing price), was as set forth on the table below:

In fiscal year 2021, our LTI included Awards of PRSUs under the 2017 Stock Plan (the “2021 PRSU Awards”) which represented the right to receive shares of the Company’s common stock (the “2021 Target Shares”) upon the satisfaction of a cumulative adjusted EBITDA measure (“2021 PRSU EBITDA”), weighted 75% and cumulative revenue, weighted 25%, each based on a cumulative three-year period, comprised of fiscal years 2021 through 2023 and subject to continued employment. Both performance goals were established in March 2021 and were not adjusted for any other factors.

The definition of 2021 PRSU EBITDA was substantially the same as the definition of 2023 AIP EBITDA (as indicated above). Revenue for the purposes of the 2021 PRSU Awards, was revenue, as determined by GAAP. Under the 2021 PRSU Awards, a threshold level of performance would have resulted in vesting of 50% of the 2021 Target Shares, a target level of performance would have resulted in vesting at 100% of the 2021 Target Shares, and the maximum opportunity would have resulted in vesting of 200% of the 2021 Target Shares. Any payout percentage between each of threshold and target payout and between target and maximum payout would be based on straight-line (linear) interpolations. Each metric was considered independently, and payout for that metric was weighted according to the weighting associated with the metric. A table summarizing the plan design for the 2021 PRSU Awards is set forth below:

Actual results for the cumulative performance period, calculated in accordance with the 2021 PRSU Awards and as certified by the Compensation Committee on April 3, 2024 were 2021 PRSU EBITDA of $275.7 million and Revenue of $4.665 billion. As these results were both below the threshold set under the 2021 PRSU Awards, no 2021 Target Shares were earned and the awards expired unvested. The Committee did not adjust the performance goals or exercise any discretion in determining that no shares were earned under the 2021 PRSU Awards.

We provide our named executive officers with certain limited perquisites and other personal benefits that the Compensation Committee deems reasonable and consistent with our overall compensation program or necessary to achieve certain executive hire and retention objectives. For fiscal year 2023, these perquisites included the opportunity for each named executive officer to receive an annual physical examination at our expense, which is

intended to promote proactive management of executive health, and the opportunity to receive the same discounts on Lands’ End merchandise that are extended to all Lands’ End employees.

The Lands’ End, Inc. Retirement Plan (the “Retirement Plan”) allows participants to contribute towards retirement (including catch-up contributions) on a pre-tax basis, subject to Internal Revenue Service annual contribution limits. The Retirement Plan allows Roth-after-tax contributions as well as pre-tax contributions of up to 75% of eligible compensation (or the limit determined by the Internal Revenue Service). We also make matching contributions to the Retirement Plan in an amount equal to 50% of the participant’s first 6% of contributions, starting the first day of the first full calendar month following one year of service by the participant.

We provide severance benefits to our named executive officers pursuant to executive severance agreements each has entered into with Lands’ End. The executive severance agreements help us attract and retain executives in a talent marketplace where severance provisions are commonly offered, while protecting our interests through post-employment non-disclosure, non-solicitation and non-competition restrictions. Under the executive severance agreements, subject to the executive’s execution of a release of claims against the Company and its affiliates, severance benefits are provided for involuntary termination by Lands’ End without “Cause” (as defined in each executive’s agreement) or termination by the executive officer for “Good Reason” (as defined in each executive’s agreement). See “—Potential Payments upon Termination of Employment” below for additional details on the terms, conditions and benefits received under a qualifying termination under the executive severance agreements.

Awards under an annual or a long-term incentive program are payable to a certain extent in the event of a termination of employment as a result of death or disability during a performance period if certain conditions are met. See “—Potential Payments upon Termination of Employment” below for additional information.

Under the Lands’ End, Inc. the 2017 Stock Plan, following a Change in Control (as defined in the 2017 Stock Plan) involving the Company, any non-vested portion of a participant’s award will fully vest in the event that either (1) the surviving, continuing, successor, or purchasing entity fails to assume or continue our rights and obligations under such award or fails to provide the participant with a substantially equivalent award, or (2) the participant’s employment is terminated within 18 months following the Change in Control on account of a termination by the Company (or any acquiring entity) for any reason other than Cause or on account of a participant’s resignation for Good Reason (each as defined in the 2017 Stock Plan). This type of treatment of equity following a Change in Control is referred to as a “double trigger” change-in-control provision and is intended to provide the participant with reasonable assurance regarding previously awarded compensation in the event of a Change in Control and subsequent termination of employment.

The Committee believes that, in order to retain valuable executives and attract qualified candidates, we must offer executive compensation arrangements that include components that are set at levels that candidates would view favorably when considering alternative employment opportunities. In making compensation decisions, we take many factors into account, including competitive considerations; the responsibilities, impact and importance of the individual’s position within the Company; individual performance; the individual’s expected future contributions to the Company; the individual’s historical compensation; the performance of the Company overall; retention risk; experience; internal pay equity; and the effect on our general and administrative expenses. The Committee also takes into account compensation and market data, which data primarily focuses on apparel retail companies and other related industries.

In connection with the actions taken by the Compensation Committee in fiscal year 2023, for the named executive officers, the Compensation Committee reviewed publicly available compensation data of a peer group of companies that was determined with assistance from Frederic W. Cook & Co., Inc. (“FW Cook”), the Compensation Committee’s independent compensation consultant, supplemented by survey data, when relevant public data were not available. While the Compensation Committee does not seek to establish any specific

element of compensation or total compensation at or within a prescribed range relative to its peer group of companies, it generally considers compensation arrangements to be competitive if they fall within a range of 15% above or below a market median.

The Committee typically reviews the composition of its peer group annually, prior to compensation determinations. The Committee believes that limited year-over-year change allows the Company to use a peer group that provides familiar market information and facilitates managing compensation levels and program design on a multi-year basis.

Following a peer group review that was undertaken in September 2022, and at the recommendation of FW Cook, the Peer Group for fiscal year 2023 remained substantially consistent with the prior peer group used by the Company, with the addition of three peer companies, Caleres, Citi Trends and Genesco, which were added due to their size, relevant business overlap and commonality of peers, and the deletion of Francesca’s, which had filed for bankruptcy protection.

In making its fiscal year 2023 compensation decisions, the Compensation Committee considered compensation data from the 19 peer companies set forth below (the “Peer Group”), comprised primarily of apparel retail companies and those in related industries. In comparing the relative size of the Company to the peer group median, our revenue was between the 25^th percentile and the median and market capitalization was at approximately the 25th percentile.

At our 2023 annual meeting of stockholders, approximately 91% of the votes cast supported our advisory resolution on the compensation of our executive officers named in the proxy statement for the meeting. The Compensation Committee reviewed these results and viewed them as an indicator of stockholder support for the compensation program and did not make any changes to the compensation program design for fiscal year 2023 in response to the stockholder vote outcome.

As equity compensation is an important part of our compensation philosophy, the Compensation Committee sets stock ownership guidelines, which require our senior executives accumulate and hold a meaningful level of Lands’ End stock, to establish commonality of interest with stockholders and align with best governance practices. The guidelines became effective July 31, 2018, and were updated September 13, 2021. The guidelines provide for the Chief Executive Officer to hold an amount of stock equal in value to four times base salary, Executive Vice President level employees to hold an amount of stock equal in value to two times base salary, and Senior Vice President level employees to hold an amount of stock equal in value to one times base salary. There is no prescribed time frame by which to accumulate the stock, however, until the guideline is met, executives are required to retain 50% of net after-tax shares realized upon the vesting of equity awards. Directly and indirectly beneficially owned shares are counted toward meeting the requirement. Any unvested or unearned restricted stock units and unexercised stock options are not counted toward meeting the requirement.

We conduct an annual compensation risk assessment, and have concluded that our compensation policies and practices were not reasonably likely to have a material adverse effect on us or our business. In reaching this determination, we reviewed our compensation plans, the types of awards, the risks associated with the plan designs and opportunity for metric manipulation. Factor mitigating risks identified, included:

We have adopted and maintain a Clawback Policy that applies to all employees at the Senior Vice President level and above. Per the policy, erroneously paid incentive-based compensation made to executives on or after October 2, 2023 is subject to recovery by the Company, in the event of an error relating to certain accounting restatements. If there is a restatement, and under the restated results, incentive-based compensation that was previously paid, otherwise would not have been paid (i.e. because performance goals, as restated, were not met), then the excess amounts paid in error are subject to recovery by the Company. In accordance with the policy, Lands’ End may not indemnify or reimburse any clawback amounts, and executives have acknowledged waiver of indemnification rights in connection with clawbacks. Our AIP, the Long-Term Incentive Program (as Amended and Restated), the 2014 Stock Plan (as Amended and Restated) and the 2017 Stock Plan also contain executive compensation recovery provisions and permit reimbursement from participating executives, to the extent required by the policy and as permitted by applicable law.

In reviewing our compensation programs, the Compensation Committee considers both the accounting treatment and the tax deductibility of compensation. However, in order to attract, retain, and motivate senior executives it is likely that we will pay compensation that is not tax deductible or may create an adverse accounting charge. Our Compensation Committee will continue to structure our compensation program in the best long-term interests of our stockholders, with the accounting treatment and the tax deductibility of compensation being among a variety of considerations taken into account.

The Compensation Committee is appointed by the Board to fulfill the Board’s responsibilities relating to the compensation of our Chief Executive Officer and our other senior executives reporting to the CEO, and equity awards for other Section 16 officers. The Compensation Committee has overall responsibility for approving and evaluating all compensation plans and our policies and programs as they affect our senior executives. For additional information regarding the role of our Compensation Committee, see “Corporate Governance— Committees of the Board—Compensation Committee.” In fulfilling its responsibilities, the Compensation Committee may retain compensation consultants to assist in structuring and evaluating executive compensation. The Compensation Committee has the sole authority to retain and terminate all compensation consultants and has the sole authority to approve the consultant’s fees and the terms and conditions of the consultant’s retention. The Compensation Committee also has authority to obtain advice and assistance from internal and external legal, accounting, and other advisors.

The Compensation Committee has retained FW Cook as its independent compensation consultant. FW Cook assists the Compensation Committee and works on its behalf on matters related to the Compensation Committee’s purposes and responsibilities as set forth in the Compensation Committee Charter. FW Cook periodically advises the Compensation Committee as to trends in executive compensation and also provides specialized studies or advice as requested with respect to executive compensation issues. In fiscal year 2023, FW Cook provided an update of compensation trends and regulatory developments, analyzed our use of various compensation elements, provided assistance with the review and design of our incentive compensation programs, assessed the competitiveness of our executive compensation levels, reviewed non-employee director compensation for the Nominating and Corporate Governance Committee, and assisted with the preparation of our public filings with regard to executive compensation. Representatives of FW Cook attend Compensation Committee meetings in person or virtually as requested, and during fiscal year 2023, regularly attended Compensation Committee meetings.

The Compensation Committee assessed the independence of FW Cook, including reviewing information received from FW Cook that addressed factors relevant to SEC and the Nasdaq Stock Market listing rules regarding conflicts of interest and independence and considers FW Cook to be independent under the applicable standards.

The Compensation Committee also received advice and considered the recommendations of Mr. McLean in fiscal year 2023 regarding the forms and the amounts of compensation for our employees, including the other named executive officers, and of Mr. McCracken, Mr. Gray and our Chief Human Resources Officer, regarding our compensation programs generally. No member of management was present during any Compensation Committee deliberations or voting with respect to their specific compensation.

The Compensation Committee reviewed and discussed the Compensation Discussion and Analysis contained in this Proxy Statement with management of the Company. Based on the review and discussion, the Compensation Committee recommended to the Board that the Compensation Discussion and Analysis be included in our Annual Report on Form 10-K for the fiscal year ended February 2, 2024, and in this Proxy Statement.

During fiscal year 2023, none of the members of the Compensation Committee was or is a current or former officer or employee of the Company. No executive officer of the Company served or serves on the compensation committee (or other board committee performing equivalent functions) or on the board of directors of any company that employed or employs any member of the Compensation Committee or any entity that has or has had one or more executive officers who served on our Board during fiscal year 2023.

The following table sets forth information concerning the total compensation paid to our principal executive officer and our principal financial officer during fiscal year 2023, our other executive officers for fiscal year 2023 who were executive officers at the end of the fiscal year and one additional individual who would have been one of the three other most highly compensated executive officers but for the fact she was not serving as an executive officer at the end of the fiscal year (collectively, the “named executive officers”). Fiscal year 2023 included 53 weeks, and accordingly all figures reflect amounts that are slightly higher than would have been the case in a 52-week year, on which basis “annual” compensation is determined. Total compensation for the 2021 and 2022 fiscal years is provided only if such person was a named executive officer in either of those years.

The following table sets forth the awards granted to our named executive officers in fiscal year 2023 under our incentive plans.

The following table sets forth information regarding the outstanding equity awards held by the named executive officers as of February 2, 2024, the last trading day of fiscal year 2023.

None of our named executive officers exercised any stock options during fiscal year 2023. The following table provides information for each of our named executive officers regarding vesting of RSU awards during fiscal year 2023.

Certain components of the compensation paid to our named executive officers reflected in the Summary Compensation Table and the Grants of Plan-Based Awards table are based on our named executive officers’ employment letters or arrangements that provide for their employment with Lands’ End. Set forth below are summary descriptions of the key terms of compensation for each named executive officer relating to their compensation in fiscal year 2023. For a discussion of the severance payments and other benefits payable in connection with a qualifying termination of employment under each named executive officer’s executive severance agreement, see “ —Potential Payments upon Termination of Employment” below and also “Compensation Discussion and Analysis” above.

Mr. McLean’s employment arrangements with the Company provide him with the following compensation: (1) a minimum annual base salary of $1,050,000; (2) an annual target bonus opportunity under the AIP equal to 100% of his annual base salary; (3) an annual target long-term incentive award opportunity equal to $2,520,000; (4) a sign-on grant of 115,633 restricted stock units (the “McLean sign-on RSU”), and a sign-on grant of options to purchase 168,081 shares of Company common stock with an exercise price equal to $10.81 per share, the closing price of a share of Company common stock on the grant date (and Mr. McLean’s start date), November 1, 2022 (the “McLean sign-on stock option” and together with the McLean sign-on RSU, the “McLean sign-on awards”), in each case which vest 25%, 25%, 50% per year, respectively, on each of the first three anniversaries of the grant date, subject to his continued employment; provided that on his earlier termination by the Company without cause or his resignation with good reason, any portion of the McLean sign-on awards that would have become vested within the 12 months following the date of separation from service will become immediately vested, and in the event of termination due to death or disability, 50% of the sign-on RSU and 100% of the sign-on stock option, respectively, that is not then vested, shall become vested; (5) a lump sum cash bonus make-whole payment of $600,000; and (6) through April 30, 2023, he received temporary corporate housing in the Madison, Wisconsin area and reimbursement of airfare between Wisconsin and his residences in New York and Maine, as well as reimbursement of certain legal fees. Mr. McLean’s primary workplace location is Dodgeville, Wisconsin and he maintains a residence in Wisconsin. Mr. McLean received the sign-on awards and cash sign-on award to replace amounts forfeited when leaving his prior employment.

Mr. McCracken’s employment arrangements with the Company provide him with the following compensation: (1) an annual base salary of $525,000; (2) a target bonus opportunity under the AIP equal to 75% of his annual base salary; and (3) a target long-term incentive opportunity, which for future awards is expected to be 110% of his annual base salary (previously 50%).

Mr. Gray’s arrangements with the Company provide him with the following compensation: (1) an annual base salary of $675,000; (2) a target bonus opportunity under the AIP equal to 75% of his annual base salary; and (3) a target long-term incentive opportunity of 110% of his annual base salary.

Ms. Rieger's employment arrangement with the Company provide her with the following compensation: (1) an annual base salary of $500,000, (2) a target bonus opportunity under the AIP equal to 75% of her annual base salary; and (3) a target long-term incentive opportunity of 110% of her annual base salary.

Ms. Rasmusen, our former Chief Innovation Officer, served the Company from November 2017 to September 5, 2023. Prior to her departure, Ms. Rasmusen was provided with the following compensation: (1) an annual base salary of $472,770, (2) a target bonus opportunity under the AIP equal to 75% of her annual base salary; and (3) a target long-term incentive opportunity of 110% of her annual base salary. Ms. Rasmusen’s employment ceased on September 5, 2023, in connection with a position elimination by the Company. In connection with her departure, Ms. Rasmusen is eligible to receive payments and benefits under and subject to her executive severance agreement with the Company, specifically, (1) salary continuation for up to 12 months, (2) continued health insurance coverage for up to 12 months, (3) 12 months of outplacement services, and (4) a lump sum payment equal to unused vacation pay.

As described under “—Compensation Discussion and Analysis—Other Compensation Elements— Severance Benefits” above, the Company is party to severance agreements with each of the named executive officers. The following is a discussion of the potential compensation and benefits that the named executive officers would be entitled to upon termination of employment. Ms. Rasmusen’s employment ceased September 5, 2023; see “— Employment Arrangements —Sarah Rasmusen” above for details concerning the compensation and benefits that Ms. Rasmusen received in connection with her departure from the Company.

For purposes of the severance agreements (except as noted) the following definitions apply:

A termination by the executive officer is for “Good Reason” generally if it results from (1) a reduction of more than 10% in the sum of the executive officer’s annual base salary and target AIP award; (2) an executive officer’s mandatory relocation to an office more than 50 miles from the primary location at which the executive officer is required to perform their duties; or

(3) any action or inaction that constitutes a material breach under the severance agreement, including the failure of a successor company to assume or fulfill the obligations under the severance agreement. Under Mr. McLean’s and Mr. Gray’s agreements, material diminution in their duties also constitutes a Good Reason, and under Mr. McLean’s agreement, a Good Reason further includes (i) no longer being the principal executive officer of the Company and (ii) if at any time that ESL Investments, Inc. and its affiliate entities beneficially own more than twenty percent (20%) of our shares entitled to vote for directors, and they, in whole or in part, vote against Mr. McLean’s reelection to the Board while he is serving as the Chief Executive Officer of the Company.

“Cause” generally is defined as (1) a material breach by the executive officer, other than due to incapacity due to a disability, of the executive officer’s duties and responsibilities which breach is demonstrably willful and deliberate on the executive officer’s part, is committed in bad faith or without reasonable belief that such breach is in the best interests of the Company (or its affiliates) and such breach is not remedied by the executive officer in a reasonable period of time after receipt of written notice from the Company specifying such breach; (2) the commission by the executive officer of a felony (in certain cases defined as a felony involving moral turpitude); or (3) dishonesty or willful misconduct in connection with the executive officer’s employment.

Subject to their execution of a release of claims against the Company and its affiliates, if the executive’s employment is terminated by the Company without Cause or by the executive for Good Reason, the executive will be entitled to receive, subject to the terms of the applicable agreement, 12 months of base salary at the rate

in effect as of the date of termination, other than for Mr. McLean, who is entitled to a payment equal to two times the sum of his base salary plus his average bonus paid for the most recent prior two completed fiscal years (“Average Bonus”), paid in installments over 24 months, and Mr. Gray who is entitled to a payment equal to his base salary plus his Average Bonus payable over 12 months. In the event the termination occurs in contemplation of or within two years after a Change in Control of the Company, Mr. McLean’s severance payment is increased to two and one half times the sum of his base salary plus Average Bonus (as defined in the Executive Severance Agreement), paid in installments over 30 months, and Mr. Gray is entitled to receive an amount equal to two times the sum of his base salary plus Average Bonus over a period of 24 months. Mr. McLean and Mr. Gray are each entitled to continued health insurance coverage for up to the same period of time as severance is paid. If termination of employment occurs during the last six months of the applicable fiscal year, Mr. McLean and Mr. Gray are also entitled to a pro-rata bonus for that fiscal year, based on actual performance.

The executives are entitled to receive continuation of the active medical and dental coverage that the named executive officer was eligible to participate in prior to the end of employment during the salary continuation period, provided that if the executive becomes eligible to participate in another medical or dental benefit plan through another employer or spousal plan during such period, the executive will be required to pay the full premium applicable to continuation coverage under the Consolidated Omnibus Budget Reconciliation Act (COBRA).

The executives also are entitled to reasonable outplacement services, mutually agreed to by the Company and the named executive officer, for a period of up to 12 months or until subsequent employment is obtained, whichever occurs first.

Per their severance agreements, the named executive officers are entitled to a lump sum payment of unused vacation pay benefits granted to the named executive officer prior to their termination date.

An eligible named executive officer will not be entitled to a severance payment under the severance agreements in the event of termination for Cause or voluntary termination.

Under the severance agreements, the named executive officers agree to, and payments under the agreements are subject to, non-disclosure of confidential information (two years), non-disparagement (two years),non-solicitation (18 months) and non-compete (generally 12 months, where permissible under applicable state law, and subject to waiver by the Company; 24 months in the case of Mr. McLean) covenants, as well as a release of liability for certain claims against the Company.

The severance agreements do not provide for payments to the participating named executive officers upon termination of employment due to death, disability or retirement. Our incentive programs and/or award agreements thereunder provide for eligibility to receive payments or vesting of awards upon the death or disability of named executive officers (and in certain cases, upon termination of employment by the Company without Cause or by the executive for Good Reason) as provided below.

Named executive officers are not entitled to any “golden parachute” excise tax gross-up payments under any plan or agreement with the Company.

As described under “—Compensation, Discussion and Analysis” above, the Company provides annual and long-term incentive awards to our named executive officers. Payments under these programs for termination of employment are treated as described below.

Annual Incentive Plan. Generally, if a participant in the AIP voluntarily terminates employment (for any reason other than disability) or is involuntarily terminated for any reason (other than death) prior to the payment date for an AIP award, he or she will forfeit their AIP award. In the event of death or disability, the named executive officer will be entitled to a pro rata payment through the termination date if the financial criteria under the AIP are satisfied. In the case of each of Mr. McLean and Mr. Gray, per each individual’s Executive Severance Agreement, in the event his employment is terminated without Cause or he terminates his employment for Good Reason, within the last six months of a fiscal year, he will be entitled to a pro rata bonus that would otherwise be payable under the AIP for such fiscal year based on actual results for the fiscal year.

2017 Stock Plan Awards. Generally, if any named executive officer voluntarily terminates employment (for any reason other than disability) or is involuntary terminated for any reason (other than death) he or she will forfeit any unvested awards made under the 2017 Stock Plan. Following the 12-month anniversary of the grant date of their award, if any named executive officer’s employment is terminated because of (1) death, the unvested portion of their award will vest on a pro rata basis through the date of death, payable in cash to their estate, or (2) disability, the unvested portion of their award will vest on a pro rata basis through the date of termination.

Provisions in Equity Awards. Under the terms of the grant agreements governing Mr. McLean’s sign-on RSUs and sign-on stock options, in the event of termination due to death or disability, 50% of any then unvested sign-on RSUs will vest and 100% of any unvested sign-on stock options will vest.

Change in Control Provisions of the 2017 Stock Plan. The 2017 Stock Plan, which govern the equity awards discussed above, provide that, except to the extent specified in the applicable award agreement, upon a change in control involving the Company, any non-vested portion of a named executive officer’s award will fully vest in the event that either (1) the surviving, continuing, successor, or purchasing entity fails to assume or continue our rights and obligations under such award or fails to provide the participant with a substantially equivalent award, or (2) the participant’s employment is terminated within 18 months following the change in control on account of a termination by the Company (or any acquiring entity) for any reason other than Cause or on account of a named executive officer’s resignation for Good Reason.

The table below summarizes the potential payouts to the named executive officers (other than Ms. Rasmusen, whose employment ceased September 5, 2023) in the event of certain termination events. The amounts shown in the following table assume that the termination of employment occurred on February 2, 2024. The actual amounts that would be paid to the named executive officers can only be determined at the time of such executive’s separation.