#1TRADING <co> Investor Presentation Second Quarter 2021 September 3, 2021#2Disclaimer Forward-Looking Statements This presentation dated September 3, 2021 includes "forward-looking statements" within the meaning of the Private Securities Litigation Reform Act of 1995. All statements, other than statements of historical facts included in this presentation, including statements concerning Duluth Holdings Inc.'s (dba Duluth Trading Company) ("Duluth Trading" or the "Company") plans, objectives, goals, beliefs, business strategies, future events, business conditions, its results of operations, financial position and its business outlook, business trends and certain other information herein are forward-looking statements, including its ability to execute on its growth strategies. You can identify forward-looking statements by the use of words such as "may," "might," "will," "should," "expect," "plan," "anticipate," "could," "believe," "estimate," "project," "target," "predict," "intend," "future," "budget," "goals," "potential," "continue," "design," "objective," "would" and other similar expressions. The forward-looking statements are not historical facts, and are based upon Duluth Trading's current expectations, beliefs, estimates, and projections, and various assumptions, many of which, by their nature, are inherently uncertain and beyond Duluth Trading's control. Duluth Trading's expectations, beliefs and projections are expressed in good faith, and Duluth Trading believes there is a reasonable basis for them. However, there can be no assurance that management's expectations, beliefs, estimates, and projections will be achieved and actual results may vary materially from what is expressed in or indicated by the forward-looking statements. Forward-looking statements are subject to risks and uncertainties that could cause actual performance or results to differ materially from those expressed in the forward-looking statements, including, among others, the risks, uncertainties, and factors set forth under Part 1, Item 1A "Risk Factors" in Duluth Trading's Annual Report on Form 10-K filed with the SEC on March 26, 2021, and other factors as may be periodically described in Duluth Trading's subsequent filings with the SEC. Forward-looking statements speak only as of the date the statements are made. Duluth Trading assumes no obligation to update forward-looking statements to reflect actual results, subsequent events or circumstances or other changes affecting forward- looking information except to the extent required by applicable securities laws. Non-GAAP Measurements TRADING Management believes that non-GAAP financial measures may be useful in certain instances to provide additional meaningful comparisons between current results and results in prior operating periods. Within this presentation, reference is made to adjusted earnings before interest, taxes, depreciation and amortization (EBITDA) and Free Cash Flow. See Appendix Table "Adjusted EBITDA," for a reconciliation of net income to EBITDA and EBITDA to Adjusted EBITDA and "Free Cash Flow" for a reconciliation of Net cash provided by operating activities to Free Cash Flow. Adjusted EBITDA is a metric used by management and frequently used by the financial community, which provides insight into an organization's operating trends and facilitates comparisons between peer companies, since interest, taxes, depreciation and amortization can differ greatly between organizations as a result of differing capital structures and tax strategies. Adjusted EBITDA excludes certain items, such as stock-based compensation. Management believes Free Cash Flow is a useful measure of performance as an indication of an organization's financial strength and provides additional perspective on the ability to efficiently use capital in executing growth strategies. Free Cash Flow is used to facilitate a comparison of operating performance on a consistent basis from period-to-period and the ability to generate cash. Free Cash Flow is defined as net cash provided by operating activities less purchase of property and equipment and capital contributions towards build-to-suit stores. The Company provides this information to investors to assist in comparisons of past, present and future operating results and to assist in highlighting the results of on-going operations. While the Company's management believes that non-GAAP measurements are useful supplemental information, such adjusted results are not intended to replace the Company's GAAP financial results and should be read in conjunction with those GAAP results. September 3, 2021 2#3HD Introduction to Duluth Trading Co.#4● ● Duluth Trading Co. at a Glance ● Workwear Heritage is the Foundation of our Authentic, Everyday Lifestyle Platform of Brands • Humorous and Distinctive Marketing. Long History of Product Innovation and Solution-Based Design. Outstanding and Engaging Customer Experience Nationwide Omnichannel Presence with Controlled Distribution September 3, 2021 ADING (CO DOUBLE FLEX" BALLROOM JEANS FIND YOUR INNER FLEX CANAVANEVAG MEN'S GEAR TRADING ULUTH TRADING com WONEN Bestsellers shirts Pants underwaterwear Peter Accessones es Gens & Gear SALE DULUTH WORKWEAR Sua Castane Senica Storm Syed WHAT AVERAGE UNDERWEAR FEELS LIKE GET BUCK NAKED Bomu, king under the co -GRIPPY LIKE A BIG BAD BOAR $39.50 WILD BOAR MOCS GET A PAIR Ⓒ A REAL MAN'S Soch SHPALLET My ATENS 335.63 Wild Boar Mess FREE DATI THE LONG & SHORT OF IT SHOP SHORTS BY INSEAM 4#5● Investment Highlights TRADING Growing lifestyle platform of brands with well-established digitally-led Omnichannel business. Multiple revenue growth opportunities ➤ Lead with a digital-first mindset ▸ Intensify efforts to optimize our owned DTC channels. > Evolve our multi-brand platform as a new pathway to grow the business. ➤ Test and learn to unlock long-term growth potential ➤ Increase and, in some areas, accelerate investments to future proof the business Strategic investments support long-term EBITDA margin expansion Generating positive cash flow with a strong balance sheet September 3, 2021 5#6Second Quarter Ended August 1, 2021 ● Financial Highlights Q2 Net sales of $149.1M increased 8.6% compared to Q2 2020, and increased 22.3% compared to Q2 2019 ● Direct-to-consumer net sales of $85.2M decreased -15.2% compared to Q2 2020, and increased 41.5% compared to Q2 2019 Retail net sales of $63.9M increased 73.6% compared to Q2 2020, and increased 3.5% compared to Q2 2019 Q2 Adjusted EBITDA of $21.6M increased $4.8M compared to the prior year second quarter Year to date free cash flow positive of $21.5M, compared to negative -$22.0M in the prior year period September 3, 2021 TRADING 6#7Net Sales and Adjusted EBITDA Strong track record of 15% Net Sales and 13% Adjusted EBITDA growth Strategic investments and operating efficiencies support long-term objectives of accelerated earnings growth ($ in millions) 304 Net Sales 376 FY15-21 CAGR = 15% 471 616 639 568 715 2015 2016 2017 2018 2019 2020 2021* *2021 reflects the high end of full year guidance ($ in millions) 34 September 3, 2021 Adjusted EBITDA ¹ FY15-21 CAGR = 13% 41 46 TRADING 52 52 55 72 2015 2016 2017 2018 2019 2020 2021* 1 Adjusted to reflect the add-back of stock compensation expense. 7#8X z Ro JD J Growth Strategy#9"Big Dam Blueprint" Growth Strategies 1 Lead With a Digital-First Mindset 2 Intensify Efforts to Optimize Our Owned DTC Channels CLIMB COMPORTAR CORMINA FIRE HOSE INTUNG CROUCH OUCH PROJ 3 Evolve Our Multi- Brand Platform as a New Pathway to Grow the Business BALLROOM JEANS LEGENDARY FINE NOSE DURABILITY FLEX FIRE HOSE CARPENTER September 3, 2021 4 Test & Learn to Unlock Long- Term Growth Potential TRADING 5 Increase/ Accelerate Investments to Future Proof the Business 9#10Lead With a Digital-First Mindset 1 TRADING Transform Duluth into a digitally-led organization integrating data and digital technology into all areas of our business, fundamentally changing how we operate and deliver value to customers. Our digital transformation will provide the structure for how we prioritize our short, mid, and long-term efforts, investments, and overall operations of the business. We will deepen relationships and build brand loyalty with our customer primarily through digital experiences. Focus on more active, personalized engagement achieved through leveraging first- party data and one-on-one communication based on customer preferences, informed by data that is shared by customers throughout the value exchange cycle. We will digitally enable operations to stay competitive, improve efficiency and deliver value creating results. September 3, 2021 10#11Intensify Efforts to Optimize Our Owned DTC Channels 2 ● ● TRADING Increase our focus and investments in our direct channel as our primary growth vehicle Our customer places a high value on our stores and they will continue to serve as a critical piece of the omnichannel ecosystem: Convenient touchpoint for services like buy online pick-up in store/curbside, ship to store, and returns & exchanges Stores play an important role in servicing business needs, such as online fulfillment We are conducting research to better inform our future store decisions including location and size: Market research will provide better insight into the size and composition of markets and the opportunity to capture share Identify what the store of the future should look like at Duluth to best serve the needs of our customers and deliver sustainable growth and profitability Refine store "selling & service" model to drive continuous improvements in key KPI's September 3, 2021 11