JANUARY 6260623 Investor Presentation

2 This presentation contains forward - looking statements that involve risks and uncertainties, including statements regarding the C ompany’s opportunities for growth and value creation, ability to build, positioning for long long - term success, focus on growing and retaining its customer base, ability to capitalize on its strengths, simplify its approa ch and drive profitability, the potential of new customers and prospect, understanding of customer needs, ability to retain customers, efficiency of targeted print and digital campaigns, ability to leverage customer pu rchasing history, first party online interactions, and third party behaviors and demographics, providing a great shopping experience, continued digital innovation by way of artificial intelligence & machine learning, enh anc ed mobile customer experience, and strategic infrastructure advancements, projections relating customer care and self - service, continued shifts of commerce and social shopping increases, plans for the Company’s Ent erprise Order Management system, Warehouse Management System and PLM and their projected impact, focus on driving brand expansion and profitability, the ability to find partners who can accelerate brand r eac h, minimize capital expense and drive profitability, the pursuit of growth opportunities and licensing, the ability to expand on third party online marketplaces and build collaborations to drive engagement with new and ex isting customers, opportunities for growth and value creation, leveraging data and analytics to engage existing and new customers, and the Company’s positioning for long term success. The following important factors and u nce rtainties, among others, could cause actual results to differ materially from those described in these forward - looking statements: global supply chain challenges have resulted in a significant increase in inbound transportation costs and delays in receiving product over the past year; further disruption in the Company’s supply chain, including with respect to its distribution centers, third - party manufacturing partners and logistics partners, caused by limits in freight capacity, increases in transportation costs, port congestion, other logistics constraints, and closure of certain manufacturing facilities and production lines due to COVID - 19 an d other global economic conditions; the impact of global economic conditions, including inflation, on consumer discretionary spending; the impact of COVID - 19 on operations, customer demand and the Company’s supply ch ain, as well as its consolidated results of operation, financial position and cash flows; the Company may be unsuccessful in implementing its strategic initiatives, or its initiatives may not have their desired impa ct on its business; the Company’s ability to offer merchandise and services that customers want to purchase; changes in customer preference from the Company’s branded merchandise; the Company’s results may be materially impa cte d if tariffs on imports to the United States increase and it is unable to offset the increased costs from current or future tariffs through pricing negotiations with its vendor base, moving production out of co unt ries impacted by the tariffs, passing through a portion of the cost increases to the customer, or other savings opportunities; customers’ use of the Company’s digital platform, including customer acceptance of its efforts t o e nhance its eCommerce websites, including the Outfitters website; customer response to the Company’s marketing efforts across all types of media; the Company’s maintenance of a robust customer list; the Company’s ret ail store strategy may be unsuccessful; the Company’s Third Party channel may not develop as planned or have its desired impact; the Company’s dependence on information technology and a failure of information techno log y systems, including with respect to its eCommerce operations, or an inability to upgrade or adapt its systems; fluctuations and increases in costs of raw materials as well as fluctuations in other production and di str ibution - related costs; impairment of the Company’s relationships with its vendors; the Company’s failure to maintain the security of customer, employee or company information; the Company’s failure to compete effectively i n t he apparel industry; legal, regulatory, economic and political risks associated with international trade and those markets in which the Company conducts business and sources its merchandise; the Company’s failu re to protect or preserve the image of its brands and its intellectual property rights; increases in postage, paper and printing costs; failure by third parties who provide the Company with services in connection wit h certain aspects of its business to perform their obligations; the Company’s failure to timely and effectively obtain shipments of products from its vendors and deliver merchandise to its customers; reliance on promotion s a nd markdowns to encourage customer purchases; the Company’s failure to efficiently manage inventory levels; unseasonal or severe weather conditions; the adverse effect on the Company’s reputation if its indep end ent vendors do not use ethical business practices or comply with applicable laws and regulations; assessments for additional state taxes; incurrence of charges due to impairment of goodwill, other intangible as set s and long - lived assets; the impact on the Company’s business of adverse worldwide economic and market conditions, including inflation and other economic factors that negatively impact consumer spending on di scr etionary items; the ability of the Company’s principal stockholders to exert substantial influence over the Company; and other risks, uncertainties and factors discussed in the “Risk Factors” section of the Company ’s Annual Report on Form 10 - K for the fiscal year ended January 28, 2022. The Company intends the forward - looking statements to speak only as of the time made and does not undertake to update or revise them as more information becomes available, except as required by law. Forward Looking Statements

Lands’ End is an iconic American brand with two profitable, digitally - enabled e - commerce businesses, deep customer relationships and many opportunities for growth and value creation. Key Investment Highlights We have a tremendously loyal customer base with an average tenure of more than 18 years who come back to Lands’ End time and again for our broad product portfolio. The use o6f ou6r existing buye6r 6file (cu6r6rently ~7 million custome6rs) enables mo6re tailo6red p6roduct me6rchandising decisions and customized, automated ma6rketing campaigns enabled by machine lea6rning. Ou6r consume6r business 6reaches consume6rs whe6re they a6re: LandsEnd.com , Company sto6res and th6rough pa6rtne6rs like Kohl’s, Amazon and Ta6rget. Lands’ End Out6fitte6rs se6rves businesses o6f all sizes and ove6r 4,500 schools ac6ross the US. We are digitally driven, leveraging our proprietary data and analytics to engage existing and new - to - brand customers while building on our DTC roots. We have successfully e xecuted on our strategy to drive growth, improve profitability and invest in infrastructure , resulting in the Company realizing operating efficiencies. 2017 – 2021 US e - comme6rce Revenue CAGR o6f 7% and adjusted EBITDA CAGR o6f 20%. 2022 6results we6re a6f6fected by mac6roeconomic 6facto6rs and global supply chain dis6ruption, but Lands’ End is well - positioned for long - term success. 3

4 Our Brand Every day comfort OUR PURPOSE An American family lifestyle brand. Inspired by life lived with purpose. OUR POSITIONING Timeless Quality. Products with Purpose. Trusted Service. Family Spirit. OUR CORE VALUES Product innovation. Direct Merchant value. Functionally Superior. Inspired by a focus on customer and employee first. OUR DIFFERENCE Why we do what we do. Where we stand in the marketplace. What we do. How we do what we do.

5 Own the vacation #1 Online Retaile6r in women’s swim. #2 Online Retaile6r in total swim. Source: NPD 12 months through October 31, 2022 Own the weather We o6f6fe6r a 366rnc~f5 day oute6rwea6r collection 6featu6ring all - weathe6r p6rotection, wa6rm/wa6rme6r/wa6rmest designations, and indust6ry - leading value. #66 Online Retaile6r in coats 6fo6r the 6family. Own the fit We d 6rive loyalty and 6rebuy th6rough tops and bottoms. 40% o6f ou6r custome6rs wea6r extended sizes (plus, petite, tall, big & tall, mastectomy and mo6re). Co6re demog6raphic 6rates Lands’ End #4 in 6fit within T6rueFit’s netwo6rk o6f 10,000 b6rands. Our Competitive Advantages

6 As we embark on the next phase of our strategy, we aim to capitalize on our strengths, simplify our approach and drive profitability. Ou6r m e6rchandising st6rategy is 6focused on growing key items, categories and franchises: We lead with a d igitally - native cultu6re and app6roach. Product Digital Customer Focused on Three Strategic Pillars Swimwear Outerwear Bottoms School/Business Uniforms 94% of our online business is done with a click. We leverage data to attract and retain customers. We leverage AI to inform marketing and promotion tactics. Our conversion rate is consistently greater than 62x apparel industry norms. We are focused on growing and retaining our loyal customer base of ~7 million. Our average customer has shopped with our brand for more than 18 years.

7 Women 31% Men 16% Swim 19% Kids 4 % Home 9 % Outerwear 14 % Footwear & Accessories 7 % We m eet our customers where they are and serve the whole family. US eCommerce 63% Retail 3 % Outfitters 16% Third Party 5 % Kohl’s, Amazon and others International eCommerce 14 % Our Business US eCommerce Product Splits. All figures based on 2021 performance.

Lands’ End Outfitters provides a compelling opportunity to reach new customers. 4,500 schools cu6r6rently pa6rtne6ring with Lands’ End ac6ross the US. ~ 12% o6f US p6rivate school ma6rket. Full 6range o6f school uni6fo6rm items available. Collabo6rating with la6rge businesses to delive6r high quality uni6fo6rm solutions unde6r multi - yea6r cont6racts. 150,000 accounts cu6r6rently pa6rtne6ring with Lands’ End ac6ross the US with 22,000 unique online sto6re6f6ronts. Focus on business un i6fo6rms and othe6r customized, company - b6randed goods such as luggage, d6rinkwa6re, stationa6ry and leisu6re p6roducts. School Uniform Small & Mid - sized Businesses National Accounts Differentiation with B2B Offering 8

Our existing customers are extremely valuable to Lands’ End. Our new customers and prospects have high potential. 81% female Average age 59 College educated More affluent Married and more likely to have children at home Household income +209% vs. US population Existing customers spend +100% more in a year than new - to - brand customers. 70% female Average age 49 College educated Affluent More than half are single Less than half have children at home Fit is absolutely critical to this customer as their changing body is a primary concern. Customer Attribute Source: Acxiom, addressable US population 9 As a digital company, we target behaviors, not specific demographics. We prioritize high - value audiences rather than broad ones. We Know our Customers

Lands’ End shows up when the customer is ready to buy. New customers are primarily acquired via search channels. We retain her with relevant contacts such as catalogs and connected digital campaigns. Social is increasingly important to all customer segments at all points in the funnel. 10 90% of our marketing campaigns are engineered by machine learning. We leverage: - O ur deep customer purchase history. - F irst - party online interactions. - Third - party behaviors and demographics. CONSUMER - LED We drive highly efficient, targeted print and digital campaigns. RESPONSIVE We Know How to Meet Her and Keep Her

Continued Digital Innovation 11 ü Target gross profit optimization through continued build - out of Dynamic Promo. ü Drive cross - category shopping by interpretation of “next product to buy.” ü Integration of SKU optimization, demand forecasting and promotion planning. Artificial Intelligence & Machine Learning ü Continue to tack on capabilities of Enterprise Order Management system. ü Implementing multi - phase Warehouse Management System. ü Improve concept - to - customer timelines with planned new PLM and product development calendars. Strategic Infrastructure Advancements ü Easy order management – one click checkout, alternative payment options, easy returns. ü By 2025, 50% customer care to be sel f - service. ü Continued shift of commerce up the funnel: increased importance of social shopping and product pages. Enhanced mobile customer experience During Cyber Week 2022, LandsEnd.com converted 3x better than the industry. * *Source: Adobe Analytics & Adobe 2022 Holiday Shopping Trends & Insights Report

Expanding on third party online marketplaces: Kohls.com , Amazon, Walmart.com and Target.com .. 75% of customers reached through these partners are new to brand or reacquired after 5+ years. Pursuing international growth opportunities and licensing of non - core product offerings to accelerate brand reach, minimize capital cost and drive profitability. Building collaborations to drive engagement with new and existing customers. We are focused on driving brand expansion and profitability. 12 OUTLOOK

Global Customer File Our active customer file reached a record high in 2021 as customers came back to re - buy from categories such as swim, knits and outerwear. 4.3M Existing 1.1M New to Brand 5.4M Total 6260166 4.6M Existing 1.3M New to Brand 5.9M Total 626017 4.8M Existing 1.4M New to Brand 6.2M Total 626018 4.9M Existing 1.5M New to Brand 6.4M Total 626019 4.9M Existing 1.8M New to Brand 6.7M Total 62606260 5.2M Existing 1.9M New to Brand 7.1M Total 6260621 13

14 FY 626017 FY 626019 FY 6260621 TTM* $1.41B Total $171M Retail $259M Outfitters $179M International eCommerce $798M US eCommerce $1.64B Total $47M Retail $87M Third Party $254M Outfitters $222M International eCommerce $1.03B US eCommerce $1.58B Total $48M Retail $116M Third Party $267M Outfitters $189M International eCommerce $961M US eCommerce $1.45B Total $59M Retail $286M Outfitters $182M International eCommerce $910M US eCommerce $14M Third Party $58M Adjusted EBITDA $28M Net Income $78M Adjusted EBITDA $19M Net Income $121M Adjusted EBITDA $33M Net Income $74M Adjusted EBITDA $(2)M Net Loss Historical Revenue Performance Historical Profitability Performance Financial Profile FY 626017 FY 626019 FY 6260621 TTM* * TTM reflects results from Q4 2021 through Q3 2022. See Appendix for reconciliation of Adjusted EBITDA to Net Income.

Lands’ End is an iconic American brand with two profitable, digitally - enabled e - commerce businesses, deep customer relationships and many opportunities for growth and value creation. Key Investment Highlights We have a tremendously loyal customer base with an average tenure of more than 18 years who come back to Lands’ End time and again for our broad product portfolio. The use o6f ou6r existing buye6r 6file (cu6r6rently ~7 million custome6rs) enables mo6re tailo6red p6roduct me6rchandising decisions and customized, automated ma6rketing campaigns enabled by machine lea6rning. Ou6r consume6r business 6reaches consume6rs whe6re they a6re: LandsEnd.com , Company sto6res and th6rough pa6rtne6rs like Kohl’s, Amazon and Ta6rget. Lands’ End Out6fitte6rs se6rves businesses o6f all sizes and ove6r 4,500 schools ac6ross the US. We are digitally driven, leveraging our proprietary data and analytics to engage existing and new - to - brand customers while building on our DTC roots. We have successfully e xecuted on our strategy to drive growth, improve profitability and invest in infrastructure , resulting in the Company realizing operating efficiencies. 2017 – 2021 US e - comme6rce Revenue CAGR o6f 7% and adjusted EBITDA CAGR o6f 20%. 2022 6results we6re a6f6fected by mac6roeconomic 6facto6rs and global supply chain dis6ruption, but Lands’ End is well - positioned for long - term success. 15

APPENDIX

17 Reconciliation of Non - GAAP Measures (in millions) FY 2017 FY 2019 FY 2021 TTM* Net Income/ (loss) $28.2 $19.3 $33.4 $(2.1) Taxes (27.7) 2.1 12.6 (4.4) Interest 25.9 26.0 34.4 36.0 Depreciation 24.9 31.1 39.2 38.9 Other Adjustments 7.0 (0.6) 1.3 5.2 Adjusted EBITDA $58.3 $77.9 $120.9 $73.6 * TTM reflects results from Q4 2021 through Q3 2022 ..