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Mickey Drexler didn’t just build some of America’s most iconic fashion brands — he changed the way Americans shop and dress.
The legendary retail executive behind the rise of Gap, J.Crew, Old Navy, and Madewell has spent more than four decades turning an instinct for what people want into billion-dollar businesses. Now, he joins Fern Mallis for a candid conversation about the art of merchandising, the power of intuition, and what it really takes to build a brand that lasts.
During his 18 years at Gap, Mickey Drexler helped grow the company from $400 million to $14 billion in sales, launched GapKids, and created Old Navy, famously named after a bar he spotted in Paris. At J.Crew, he transformed the brand into a fashion powerhouse and founded Madewell, redefining American casual style along the way. Today, as chairman of Alex Mill, founded by his son Alex, he continues to champion the art of making clothes people actually want to wear.
A trusted sounding board to entrepreneurs, Drexler has never been shy about sharing an opinion or challenging conventional wisdom. Hear him talk to Mallis about how he turned Gap into a retail juggernaut, the thinking behind launching Old Navy and Madewell, what he’s learned from decades of building and reinventing brands, and how he knows what customers want before they know it themselves.
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Millard “Mickey” Drexler is the chairman of Alex Mill, the New York-based, women’s and men’s fashion brand. Founded in 2013 by Mickey’s son, Alex Drexler, Alex Mill launched with just one perfect men’s shirt that became a cult favorite. Today, the collection has evolved into a tightly edited collection of wardrobe essentials and is available nationwide online, at select retailers and in Alex Mill’s two New York City-based freestanding stores.
Previously, Drexler served as Chairman and CEO of J.Crew Group, where he grew it into a leading specialty fashion brand and founded Madewell. Prior to that, he spent eighteen years at Gap, Corp. While there, the company grew from $400 million to $14 billion dollars in sales. During his tenure, Drexler founded Old Navy, which he named after a bar he saw on Rue St. Germain in Paris and launched Gap Kids.
Drexler also served as a director and investor in Warby Parker until 2020 and was a Director of Apple Inc. from 1999 to 2015.
An expert in schmoozing and intuition, Drexler is known to be a notorious kibitzer to businesses and entrepreneurs.
The award-winning creator and organizer of Fashion Week in New York and cities across the globe, Fern Mallis has been an industry game changer in the world of fashion and design for more than 35 years. A former senior vice president of IMG Fashion and executive director of CFDA, she is the author of Fashion Lives: Fashion Icons with Fern Mallis, published by Rizzoli, which features no-holds-barred interviews, combined with never-before-seen personal photographs from interviewees such as Tom Ford, Marc Jacobs, Calvin Klein, Donna Karan, Michael Kors, Tommy Hilfiger, Betsey Johnson, Polly Mellen, Bruce Weber and more. She is currently the president of her own leading international fashion and design consultancy, Fern Mallis LLC.
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