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NEW YORK, United States — Bronx-born fashion pioneer Millard "Mickey" Drexler's first foray into the apparel industry was as a teenager, working with his father at a coat manufacturing company during the holidays.

Dexler's extensive knowledge of what sells has catapulted him to "retail king" status. He took the helm of Ann Taylor from 1980 to 1983, transforming the brand into a coveted hotspot for women's workwear in America. Later at Gap Inc., he launched Old Navy in 1994, shaking up the retail market after amassing $1 billion in annual sales in just four years. He also launched Gap Kids and oversaw the acquisition of Banana Republic.

The  companies I like are companies that have brands that one needs to have an imagination to run.

And yet, Drexler has been a fashion force to lift many brands out of troubled waters, including J.Crew: "I thought it was a great business, I loved their catalogue, I loved their style but they just didn't know how to make money." But as with many retail brands, J.Crew wasn't on top forever.

In 2017, Drexler stepped down as J.Crew chairman amid reported tensions between himself and then-Chief Executive Jim Brett, who attempted to revive the brand through the introduction of new labels, loyalty programmes and further discounting of products to offset the 15 straight quarters of losses they had experienced. Brett's year-and-a-half tenure ended in November 2019, and J.Crew is still finding its footing.

“All fashion is cyclical,” he said. “You’re guaranteed to hit a lot of walls… [but] then you sit down and figure out how to fix it. It’s not a business where you can get knocked down and say, ‘I’ve had enough.’”

In this episode of The BoF Podcast, Drexler takes Executive Editor Lauren Sherman through his career highs and lows and how he transformed multiple mass-market brands into cult hits.

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