How to thrive in today’s retail environment, according to Mickey Drexler

Secrets of success from the former head honcho of J.Crew, Old Navy, and Gap

Millard “Mickey” Drexler has worked at—and overhauled—so many household-name retail brands, he’s a household name himself in the industry. But for his next act, he’s taking on the startup world.

Arguably best known for founding Old Navy and turning J.Crew into the company it is today, Drexler is now working with his son, Alex Drexler, on Alex Mill, a startup fashion label designed by former Madewell and J.Crew designer Somsack Sikhounmuong. “There’s a need for—as silly as it sounds—really nice clothes that you don’t need to take a mortgage out to buy,” Drexler says of the label, which started as a men’s shirting line and now includes a women’s collection (with striped shirts, utility jumpsuits, and shirt dresses), all available at a relatively reasonable price. “I’m stunned at the prices around for nice quality,” he told YouTube fashion and beauty director Derek Blasberg at their recent sit-down at Made By We in New York. Alex Mill aims “to create something that we felt was missing.”

Having someone with a résumé like Mickey Drexler’s onboard isn’t the norm for most startups, but Mickey Drexler doesn’t generally follow the norm. Born and bred in the Bronx (which Blasberg noted is a low-key fashion nesting ground, with Calvin Klein and Ralph Lauren also born in the borough), Drexler says he developed an “instinct” for the business. He worked odd jobs for his father, who was in the garment industry, and landed a job right out of college at A&S department store in Brooklyn. He then went on to rise through the ranks at Bloomingdale’s, Macy’s, and A&S (again), until Gap’s Don Fisher lured him to San Francisco to revamp (and eventually, save) the company.

Drexler’s résumé is so extensive, he accidentally left out a major chapter while going through it with Blasberg. While reminiscing about his time at Gap, Drexler suddenly realized that he had been president of Ann Taylor for four years: “I forgot all about that,” he said. As one does.

But back to Gap: In his 18 years at the helm, Drexler was behind some of the company’s biggest successes (see: the famous khaki commercials) and the launch of Old Navy—which, it was announced earlier this year, is being spun off into its own public company next year. Drexler’s tenure in San Francisco also allowed him to develop a relationship with Silicon Valley’s most elusive resident: Steve Jobs.

“He said, if you join my board, I will join your board,” Drexler told Blasberg. Jobs, ever the innovator, had a specific goal in mind. “He wanted to do what Gap was doing in terms of creating his own stores.” (More on that later.)

Drexler then famously went on to J.Crew, where he was CEO from 2003 until 2017, and remained chairman until January 2019. There, he launched sister brand Madewell, a name he had previously bought off a friend for $125,000 because he “fell in love with it immediately.”

No matter which brand he’s called home, Drexler has brought his unique business sense to each of them. Here, a few nuggets of wisdom from the man himself—whether you’re diving into the startup world, launching a second (or third or fourth) act for a storied legacy brand, or simply could use some new perspective.

“If I spend a half hour with someone and I don’t learn anything, I don’t want to work with them,” Drexler (left) said.

Make sure your brand has a purpose

When Blasberg asked Drexler about the state of the fashion industry right now, he didn’t hesitate: “There’s too much of everything. Too much assortment, not enough beauty and good product.”

Alex Mill’s “about” page echoes that sentiment with a self-awareness most fashion brands—or any brands, really—lack, stating: “Nobody needs new clothes right now. But everyone needs the right clothes. So we make them.”

Ultimately, he said, it all comes down to purpose. “You have to have a vision. You have to think there’s a reason for it.”

Surround yourself with people who are smarter than you (so to speak)

“If I spend a half hour with someone and I don’t learn anything, I don’t want to work with them,” Drexler said. “I want to learn from them, I want to feel an energy.”

Steve Jobs shared a similar philosophy, according to Drexler—and that’s what made him connect. “Steve wanted to learn how to build the [Apple] stores,” he said. “A sign of good leadership is if you don’t know something, ask someone who can help you.”

Trust the data—as well as your instincts

“Numbers were always very intuitive to me. To be successful, you have to feel and read the selling reports,” he says. “But the data doesn’t create the product.”  

Success sometimes comes slowly

When J.Crew launched Madewell, Drexler said, it took six years to turn a profit. Now, like Old Navy, it’s rumored the company may spin off and file for an IPO. Simply put, he said, “it takes time, and energy, and a lot of stuff to get going.” And maybe $125,000 for the perfect name.