You’d be hard-pressed to find an executive who’s had a bigger impact on retail and apparel over the past half century than Millard “Mickey” Drexler. In the 1990s, Drexler turned the Gap from a sleepy multi-brand retailer into a juggernaut clothing brand by making office-ready button-downs and khakis comfortable enough to swing dance in. He then revitalized J.Crew, hiring legendary women’s wear director Jenna Lyons, whose ballet flats, sequins, and cashmere became the uniform for legions of women, including former first lady Michelle Obama. While overseeing those companies, Drexler also launched new ones. He founded the affordable mall staple Old Navy while at Gap, and the youthful, fashion-forward Madewell for J.Crew.

Drexler has had a hand in other companies. Steve Jobs recruited him to the Apple board, where Drexler served from 1999 to 2015, helping design the company’s retail stores. More recently, Drexler served as chairman of the board at Outdoor Voices, presiding over founder Ty Haney’s ouster.

Along the way, he became renowned for his unorthodox leadership style and uncensored pronouncements. An unapologetic micromanager—“The world needs more micromanagers,” he told CNBC in 2012—he was known for using an office-wide PA system to summon employees while at J.Crew.

These days, he’s most often found at the offices of Alex Mill, the 11-year-old clothing company founded by (and named after) his son. Drexler serves as chairman of the workwear-inspired brand, which sells direct-to-consumer online and in two Manhattan storefronts. Though Roxanne Stahl O’Hara took over from Drexler as CEO earlier this year, Drexler is still known for making sure that Alex Mill’s 27 full-time employees are in their seats each morning (he’s not a fan of WFH) and involved enough to obsessively check the brand’s daily sales data.

Fast Company caught up with Drexler on a late-November morning at Alex Mill’s Soho offices to talk about his career and the future of retail. Dressed in his signature uniform, which includes a white button-down shirt, paisley Drake’s of London scarf, and Alden shoes (ordered for him by former J.Crew menswear director Todd Snyder), he sat for a far-ranging—and digression-filled—conversation that stretched from its originally allotted hour to well past two. He talked about the early days at Gap, what’s next for Alex Mill, working with Steve Jobs, and his appreciation for Erewhon stores, though he’s never stepped foot inside one.

This conversation has been edited and condensed for clarity.

[Photo: Alex Mills]

We’re coming off Black Friday. Alex Mill doesn’t do a Black Friday sale. Why is that?

In this country, Black Friday is taking over retail. I heard even Apple had Black Friday. And don’t even talk to me about my old companies: If you look at their websites, everything’s half off anyway. Alex Mill didn’t do it because once you start, you can’t stop. It’s not a way to build a business. It’s a way to keep training people to wait for a sale before buying. I always hated sales. There’s no integrity in selling goods on sale because [then customers] don’t trust the company.

You ran Gap and J.Crew, which are known for their sales. Did your philosophy around discounts change?

I don’t call it a philosophy because you’ve got to change and be flexible. In our business, there’s nothing that’s a religion for me other than selling nice quality goods [at a] good value. I usually trust my gut and my instinct. And I think you have to be born with that. You also have to be born with taste, style. I don’t know why, but I have it. You can’t buy style.

Value has been a focus for many of your previous clothing brands, starting with Gap.

I always felt that there’s a market out there for cool, nice, classic-ish clothes. I used to buy Ralph Lauren wholesale because my old roommate’s cousin was Ralph’s secretary: I could afford it at half price. With Gap, I wanted to start a company [that sold] what I felt Ralph Lauren was, but more affordable. Benetton was the other inspiration.

When I started at Gap [in 1987], they sold 20 different brands. [Gap stores originally sold multiple private-label brands as well as clothing from other companies.] A third of the business was selling Levi’s. I always remember the name of [Gap’s private label] women’s jeans collection, Foxtails. When I started, [cofounder] Don Fisher would say, “Why are you offering all the markdowns?” I’d get a little emotional and I’d say, “If we don’t take the markdowns then we don’t get cash.” We needed to have a bad quarter to liquidate bad inventory.

[Photo: Alex Mills]

You’re a legend in the apparel industry, but you were also on the board of Apple for 16 years. What was it like to work with Steve Jobs?

They say I’m difficult. Steve Jobs was very difficult. He was the smartest guy in every room. But you have to be difficult. You have to have high standards. I was on the board of Apple for 16 years. I actually recommended on LinkedIn, I suggested there should be a Steve Jobs day, like how you have a Martin Luther King Day and a George Washington Day, because of what he’s done for the world. I don’t think I got many people who responded.

Why did you want to join that board?

I wasn’t a technology guy but Steve Jobs recruited me in 1999. I told him I’d join his board if he’d join Gap’s board. I wanted him to join Gap’s board because [the then-members of the board] were all prep school buddies and I knew he’d come in and be disruptive. He wanted me to help him launch retail. The first store he designed was awful; I remember saying to him that the store was fighting with the goods.

You recently said that these days there aren’t many good stores. What’s a good store to you?

I’m talking about a well-run business. I like T.J. Maxx. I think they are the biggest department store in the world. The other—I’ve heard about this but I’ve never seen one—is Erewhon. My friend was their first investor, and they had that long New York magazine article about them. I can’t read long articles.

What makes a good store?

Consistency is important in everything in my opinion, especially restaurants. People who do the best have an ownership mentality. I’ve always thought like an owner. I look at the numbers every day. Humility is also important. I didn’t identify with the fancies growing up. I’ve got a lot of wealthy friends who think they’re the smartest person in every room. More than money, success is how you treat people.

How do you think about Alex Mill’s physical retail presence?

My thinking is that opening shops is critical. We only have two shops. Our biggest challenge is to get well known. No one knows who we are. Most people love our clothes, though.

[Photo: Alex Mills]

One of your biggest successes, for a while, was hiring Jenna Lyons to run women’s wear at J.Crew. Have you been watching her on Real Housewives of New York?

I don’t want to speak about her. I can say that I couldn’t have done it without her. She was a great partner.

The other board you were on was Outdoor Voices. What was that like?

After I left J.Crew [in 2017], I was not that busy. I was sitting in a venture capital office. [Drexler started his own fund, Drexler Ventures.] I was bored. I was looking at all these bad fashion-centric companies, and I always [made] a quick decision on whatever it was. The biggest investor in Outdoor Voices asked me if I wanted to be chairman of Outdoor Voices. I jumped at it. I jumped too quickly because I didn’t spend time with the founder. What I’ll say on the record is that they had brilliant marketing. I was excited about it because I envisioned it to be a major player in the activewear world, like Lululemon. It had style. . . . There was a thing there that I liked a lot intuitively. But it was a bad choice for me. It was just a bad choice.

The fashion world—and certainly Gap and J.Crew—doesn’t have a great reputation when it comes to sustainability. How do you think about sustainability at Alex Mill?

We are sustainable, but I think if you have to talk about it, you’re really not. I interview everyone who wants to work for the company. They say they majored in sustainability. I say, “Please define it.” In the clothing business, there’s just too much stuff. We don’t overproduce at Alex Mill. I’ve learned to be conservative and sell out of items rather than make too much. Alex Mill also has a program to repurpose surplus fabric and garments.

Alex Mill is 11 years old. What comes next for the brand?

I never think about the next 10 years. In fact, I don’t know how to do five-year plans. I never did them. I don’t even know what’s gonna happen next month.

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5 thoughts on “‘You have to be difficult’: How Gap and J.Crew icon Mickey Drexler became the king of mall-brand retail”
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