Mickey Drexler: The Merchant Prince Who Built J. Crew and The Gap Takes on a New Role
One of the most well-known, well-respected voices in fashion talks about building Alex Mill one jumpsuit at a time… plus, why he’s so obsessed with buying homes… and why he hires fast walkers
Mickey Drexler is bold. Takes chances. Thinks outside the box.
And that’s just his pancake order.
When we sat down for breakfast at Sant Ambroeus on Manhattan’s Upper East Side last month, Drexler – who famously wakes up at the crack of dawn and is done with Soul Cycle by 7am – was famished.
He knew the posh Italian eatery was not known for its pancakes but was willing to give it another go. One. More. Chance.
“Just two,” he said. “Thin and crispy.” (They didn’t come thin or crispy).
Lesson learned. And Sant Ambroeus, he tells me, is working on its pancakes.
Drexler is now CEO of Alex Mill, the clothing brand founded by his son in 2012.
Before that, he took The Gap from 400 million to 14 billion. He made J.Crew cool again, like Michelle Obama cool.
He’s credited with creating Casual Fridays. He founded Old Navy and Madewell.
And he’s completely obsessed with top-tier real estate. Think Andy Warhol and Calvin Klein.
When I first profiled him for CNN ten years ago, Drexler was the CEO of J.Crew and used a loudspeaker to communicate his ideas and speak to colleagues.
Bold. Takes chances. Thinks outside the box… as you’ll soon find out.
A ROCKY CHILDHOOD: “I WANTED TO ESCAPE MY LIFE”
ALINA CHO: Born and raised in the Bronx.
MICKEY DREXLER: Yes.
Young Mickey Drexler, seated center
ALINA CHO: Mother died when you were sixteen. She had cancer — never talked about it, though.
MICKEY DREXLER: Well, in those days, they never talked about it. But she had three close sisters, so it was four of them. They all talked about it. When you're a kid, I was an only child, you know exactly what's going on. I knew.
ALINA CHO: You did know.
MICKEY DREXLER: She had breast cancer and she had a mastectomy. There was no covering up in those days. I slept in the foyer of the apartment, so we all -- the three of us -- kind-of interacted.
ALINA CHO: You had an interesting relationship with your father.
MICKEY DREXLER: Well, it wasn't a wonderful one at all, to say the least. He worked for a coat manufacturer in the garment business. He was an angry man who wanted to be successful. But always lifted himself up to a point where it was more his own idea of how important he was at work than the reality of how important he was. He had a simple job. He bought buttons and piece goods [fabrics] and talked about his boss all his time.
ALINA CHO: But he did have this sense of style.
MICKEY DREXLER: Well, he did. He was well dressed. He cared.
ALINA CHO: If your mother died when you were very young and your father never realized his dreams, where do you think you got your drive?
MICKEY DREXLER: Well, I think part of it comes from trying to not be him [my father]. I wanted to escape my life. I did not like being at home. I just was very lonely, and I didn’t want to be there. The drive probably came from wanting to escape, wanting to be successful, wanting to be liked, [wanting] to be recognized. I didn't say, "I'm driven." I never felt that way.
STARTING IN FASHION: “IT’S ABOUT GOOD PRODUCT”
MICKEY DREXLER: I worked at Abraham & Straus — now Macy's — in Brooklyn, for a summer job, $125 a week. I loved it. I worked in the young men's jeans department. I was running to the stockrooms. I liked the action.
ALINA CHO: You loved it.
MICKEY DREXLER: This is interesting. Thank God it happened. A friend of mine, I fixed him up with the head of HR. They offered him a job, $11,500. They offered me $11,000 a year. I went crazy. It was incredibly not smart on their part, but it was an incredible way to say I'm not as good as him after I worked there for three months.
ALINA CHO: So, what did you do?
MICKEY DREXLER: I went to work at Bloomingdale's. They paid me $11,500, by the way. I didn't ask for it.
ALINA CHO: You got what you were worth.
MICKEY DREXLER: That's right. Because I identified with my dad, who was complaining and bitter and this, that, and the other thing. Now, it's going to happen to me in my life? I didn't know that then, but you look back and you figure it out.
ALINA CHO: Of course.
MICKEY DREXLER: First day, I was in housewares. I didn't know what the hell was going on.
ALINA CHO: Housewares?
MICKEY DREXLER: I didn't know a pot or a pan from this and that. The next morning, Stan Stern, who was my first boss, said, "We're putting you into the sportswear department because the buyer is on maternity leave." There I was, second day, the boss. I was the buyer. I was buying. I was going into the market. I was on my own.
ALINA CHO: And what did you learn?
MICKEY DREXLER: I learned all the things you need to learn about a business. It's about the product. It's about good product. It's about things that sell well. The bestsellers drove the business.
BEING CEO AGAIN: “WHICH WAY IS THE PUCK GOING?”
ALINA CHO: Let’s talk about Alex Mill, the company your son started in 2012.
Alex Mill in Soho, New York, NY
MICKEY DREXLER: Sure.
ALINA CHO: When Alex started it, it was purely a men's company, right?
MICKEY DREXLER: It was men's shirting and t-shirts and woven shirts and kids. Then, we moved into womenswear.
ALINA CHO: I’m wearing my Alex Mill terry Benny jumpsuit.
Alex Mill Benny jumpsuit.
MICKEY DREXLER: Yep.
ALINA CHO: I really do come to you for jumpsuits.
MICKEY DREXLER: Like that jumpsuit. We have a campaign [that just came out with] jumpsuits. It's the [fifteen-second outfit].
ALINA CHO: Amazing. Smart.
MICKEY DREXLER: See, when you look at something like that, it's a matter of taking a point of view on a jumpsuit or we have a great skirt. It was done in two colors. I said, "Do it in 10, prints and stripes." It's just having an imagination and expanding.
The colorful world of Alex Mill
ALINA CHO: Do you love product?
Alex Mill
MICKEY DREXLER: Good product. We’re going to do a little section of things like cashmere socks. I'll tell you why.
ALINA CHO: I do want to know why.
MICKEY DREXLER: I'll tell you why because I'm wearing them right now. They're coming in [soon]. Once you go cashmere, even in the summer, once you go cashmere, every other sock is just not good enough. Last year, I looked for a good cashmere sock around the world online, and there’s none in the world.
ALINA CHO: I think that's so smart.
MICKEY DREXLER: Rome wasn't built in a day, and as you're trying to take a company and build and build and build it, it's step by step…
ALINA CHO: … literally product by product?
MICKEY DREXLER: Absolutely. Product by product. If you add up all the products, that's your company.
ALINA CHO: That's right.
MICKEY DREXLER: I always say, “Which way is the puck going?” It’s about product, it's about the merchandise, it's about the emotion. It's about style and taste in our book. It doesn't have to be in other books, but that's our book. That's our playbook.
WHY HE HIRES FAST WALKERS
ALINA CHO: I either read or heard that when you're looking to hire people, one thing you look at is are they a fast walker?
MICKEY DREXLER: It's an energy that people exude, and you feel it with people. Do they have the energy? Do they have the intensity? Can they sometimes interrupt you, okay, because they're in a hurry to get out what they want to say?
ALINA CHO: Well, you like people who speak up.
MICKEY DREXLER: Yeah. Fast walkers tell me they're in a hurry to get some place. It tells me they can't wait.
HIS OBSESSION WITH REAL ESTATE
ALINA CHO: In the same way that you have this eye for product, you have this eye for real estate. What's with the obsession with real estate? I mean it's been said that you grew up in a small apartment…
MICKEY DREXLER: I grew up in an apartment I always wanted to escape from. I just wanted to live in a nice place, happy place. It's kind-of weird. I found myself being able to afford to have what I wanted. It wasn't to show off or anything. It was because I loved finding good real estate in good locations.
ALINA CHO: You had a couple of homes in the Hamptons. The [Andy] Warhol estate [since sold].
Photo source: Variety
MICKEY DREXLER: Warhol.
ALINA CHO: And then you had a house in Bridgehampton, right?
MICKEY DREXLER: I still live there.
ALINA CHO: And you bought a little beach house in Amagansett. What else?
MICKEY DREXLER: Right now, we have [Upper East Side] where we've been for 15 years. We have a beautiful house in Tribeca.
ALINA CHO: And now you have Miami. You have Calvin [Klein’s] house in Miami.
MICKEY DREXLER: Well, I have three houses in Miami, but they're all together.
Source: The Wall Street Journal
ALINA CHO: You put them together.
MICKEY DREXLER: We [closed] on the third house because I don't want a neighbor.
ALINA CHO: Some people might ask, “Isn’t it easier to just stay in a hotel?”
MICKEY DREXLER: I love beautiful places. What is it? You grow up the way I did. I don't know what it is. It's just, I love beautiful places.