Mickey Drexler doesn’t like to wait for things to happen. His storied retail career, with executive roles at companies like Ann Taylor, Gap Inc., and J.Crew, was defined by a bullish leadership style and a move-fast, get-results attitude that helped catapult those businesses into American retail mammoths. Old Navy, which he launched during his time at Gap Inc. in 1994 in about 18 months, became the fastest retailer to reach $1 billion in sales in four years.
But when he joined Alex Mill as chairman in 2019 — the New York brand founded by his son, Alex, in 2012 — Mickey had to be patient. “We put the time in and the work. Now, I feel very good about where we are,” he says. “But you never can relax in this business. Because there’s always the next season, the next year.”
Alex Mill started with a simple premise — a better men’s button-down — and has grown to a full-fledged men’s and women’s fashion brand with a reputation for colorful knits and natural materials. If you blur your eyes, you might think you’re looking at J.Crew’s website as you scroll. But the secret sauce that separates Alex Mill from Mickey’s past endeavors is in the details and behind the scenes. Mickey, when he officially came on board as chairman (reporting to Alex), did so on the basis that he wouldn’t have oversight from investors — it would just be him and his son, plus Alex Mill’s creative director, Somsack Sikhounmuong, who worked with Mickey at J.Crew before he joined Alex Mill, at the helm.
“I joined [in 2019] because I frankly didn’t want to have investors anymore,” Mickey says. “Small is the new big. That’s what we always say. And actually, I love small, because big companies today are bureaucratic. There’s an ivory tower,” he says. He had closed out his time as the CEO of J.Crew in 2017 and spent two years as J.Crew’s executive chairman, as well as on the boards of other brands, including a stint as chairman of Outdoor Voices. “And if you want something done, you have to go through layers upon layers. And even then, you don’t get an answer.”
We’re sitting in a conference room at Alex Mill’s shabby-chic SoHo offices. Alex, Mickey, and Sikhounmuong, who also joined in 2019, have gathered to discuss the brand’s launch of a mini tote bag and ballet flats. It’s the next evolution of what Mickey joined to do, which was start the brand’s womenswear business after it spent the first five years dealing in men’s clothing (the first signal that there was an appetite for womenswear was when Goop bought its men’s shirts for its women’s store in 2015.) The ballet shoes are made in Florence and come in seven colors. The Perfect Little tote launches on March 10 and expands the tote category, which has become the brand’s bestseller.
It’s the Drexlers’ first joint interview discussing the business, but Mickey does most of the talking. I make sure to ask about these new products, but we don’t stay on them long. Mickey is the type of interview that makes a PR person squirm. At 81, he’s at the no-fucks stage of his career, and it’s clear he doesn’t play when it comes to Alex Mill.