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Fashion’s ‘Merchant Prince’ Mickey Drexler Takes CEO Reins Again

After a few years out of the spotlight upon retiring as CEO of J.Crew, Millard “Mickey” Drexler is back in the driver’s seat of a fashion brand yet again. At 76 years old, Drexler is taking on the CEO role at Alex Mill, the apparel brand started by his son, Alex Drexler, according to a report from the Wall Street Journal.

Mickey Drexler already had held an advisory role as executive chairman of the brand Alex founded in 2012 with the goal of “making the perfect shirt.” In 2017, the elder Drexler made an investment in the company and introduced his son to Somsack Sikhounmuong, who was then J.Crew’s chief design officer.

The next year, Alex teamed with Sikhounmuong to relaunch the Alex Mill brand for both men and women, featuring pants, jackets, outerwear, shoes and accessories within its collections. The brand was repositioned for direct-to-consumer audiences, although collections are available at retailers such as Nordstrom, Net-a-Porter and Huckberry, as well as marketplaces like Farfetch. Alex Mill operates one store in Manhattan’s SoHo district and sells men’s shirts at luxury brands including Barneys New York.

What’s more, the J.Crew legend is now making another “significant” investment through his investment fund, Drexler Ventures. Though he declined to specify the amount to the WSJ, the A-list executive said that he is the largest shareholder, followed by his son and Sikhounmuong, both who are now listed as the brand’s co-founders.

Running a brand like Alex Mill marks a change in scope for Drexler, the “Merchant Prince” who hails from a long history of specialty apparel giants and department stores. Drexler was named president of Gap Inc. in 1987 and CEO in 1995. He engineered the company’s boom in the 1990s, becoming highly influential in American fashion and launching both the Old Navy brand as well as the Gap Kids brand. The focus on basics, khakis and a robust ad campaign paid off—in the nearly two decades he worked at Gap until his departure in 2002, the retailer grew from 550 stores doing $80 million in sales to 4,000 stores valued at nearly $14 billion.

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While he was unceremoniously ousted from Gap Inc. by its board after two years of declining sales, Drexler bounced back at his next stop, J.Crew, which hired him as both chairman and CEO in 2003. At J.Crew, Drexler wanted to take the specialty apparel retailer upmarket with higher-quality products and higher price points. He also founded the successful spinoff Madewell brand in 2006, and guided J.Crew to expand its annual revenue from $700 million to $1.7 billion by the end of the decade. With the increased prices and elevated quality, J.Crew nearly tripled revenue and transformed what was largely a catalog business.

And Drexler, known for his painstaking attention to detail, even created a library at the retailer’s headquarters to document the unique hues the brand invented each season.

But the 2010s weren’t as kind to J.Crew, as the company was late to the online revolution and erratic pricing and discounting strategies plagued the chain in the wake of the Great Recession. By 2016, J.Crew was saddled with more than $2 billion debt to its private equity owners.

As customer preferences were beginning to change and both fast fashion and online shopping continued to grow, the detail-oriented Drexler admitted to the Wall Street Journal in May 2017 that he had “never seen the speed of change as it is today.” The next month, he stepped down as CEO of J.Crew, and remained chairman until January 2019.

Prior to working with Gap Inc., where he started in 1983 to oversee the company’s portfolio of brands and overhaul merchandising and store layouts, he had stints at defunct New York-based department store Abraham & Straus, as well as Macy’s and Bloomingdale’s. His first CEO role was at Ann Taylor in 1980, where he is credited with turning the women’s wear business around in his three-year stint.

Drexler has had experience in direct-to-consumer through his service on company boards—he was previously chairman of Outdoor Voices and serves as a Warby Parker board member, and invested in both companies. He even served on the board of directors at Apple from 1999 to 2015.

Now, Drexler’s focus is growing a brand known more for its updated American classics, such as $150 Oxford button-down shirts and $125 cardigan sweaters. One of Alex Mill’s signature items is a jumpsuit, the inspiration for which came while Sikhounmuong was digging through a Los Angeles vintage shop. Alex Mill’s striped tees, cotton crewneck cardigans, and plaid flannel shirts are designed to be everyday staples of a consumer’s closet.

And while the elder Drexler has the background in traditional specialty apparel retail with a focus on product, his progeny brings a completely different fashion background to the table. Alex has worked at upstart, smaller fashion brands such as Steven Alan and now-defunct contemporary label Gryphon, giving him more of a feel for building companies from the ground up. If there’s one characteristic the father-and-son duo has in common, it’s that they prefer to hear directly from customers about their purchase. At J.Crew, Mickey answered calls and emails from customers, and Alex has since followed that route. In fact, Alex told the Wall Street Journal that his design team recently tweaked the fit of a jumpsuit to make it slimmer, because some customers wrote to say it was too roomy.

The smaller scale of Alex Mill has enabled the former J.Crew chief to have some fun again, he told the Wall Street Journal, since he can focus on the details, down to the color, style and buttons of every garment.

“I never want to retire,” Drexler said.