Maybe it was the first button-up your mother bought from baby Gap, back when your infant legs couldn’t even stretch out straight.
Frantically pacing the floors inside of J. Crew as you deducted which pair of jeans would most impress your first high school crush.
Or, like I did, experiment with freshman menswear brands like Alex Mill after a baptism by fire in a city like New York, where you’re trying to maintain pace with every stylish urbanite you share the sidewalks with.
Point being, if you’re a man in America, Mickey Drexler had something to do with how you dressed at some point in your life.
After holding key roles at Abraham & Straus and Bloomingdale’s, Bronx native Millard “Mickey” Drexler’s leadership at Gap reshaped the company’s image with a successful pivot into private label merchandise and the birth of Old Navy. After that, Drexler brought a sharp focus on brand identity during his tenure at J.Crew, positioning the brand as a premium yet accessible. During this period, he spearheaded the highly successful Madewell banner that today stands as one of the most lucrative labels in the J.Crew portfolio.
Beyond his current role in fashion at his son’s brand, Alex Mill, Drexler’s expertise spans serving 17 years on Apple’s board and even making a cameo appearance in season 5 of Breaking Bad.
My first contact with Mickey was when I wrote an article about Alex Mill. In this piece, I covered their Upper East Side flagship, outlining my admiration for their clothing’s classic yet updated designs, refined quality, and endearingly simple merchandising. The write-up amateur at best, and having to pay hosting and domain fees put my portfolio-building endeavors in the red.
I sent it to his son Alex on Instagram without expecting much from the cold outreach. Six months into my new role as senior assistant planner for Bloomingdale’s, I get a call—”Hi Matt, it’s Mickey.”
My boss’s boss was an arm’s length to my left with a mere transparent Covid partition between us to buffer the dialogue. I fled to the maternity room—the only windowless room on my floor with a lock on the door—and obliged to his praise for thoughts on his son’s brand, followed by an invitation to meet the team.
If I told my work peers what had just gone down, they wouldn’t believe me. If they did believe me, I’d probably get fired out of suspicion. It was a New York moment in every sense.
But what spurred my longstanding admiration for “the merchant prince?” Simply put, it’s his old-school approach to running an apparel business.
Modern fashion companies operate under the expectation that in order to succeed, they must execute quarterly collaborations and aggressive retail expansion plans—often funded by risky venture-capital partners lacking adequate retail nuance.
Mickey, on the other hand, hasn’t lost sight of the fundamentals in retail longevity: the right assortment, thoughtful experimentation, and behind it all, as he coins “people that get it.”
With everyone wanting a piece of the industry’s clout pie, I spoke with my fellow Bloomingdale’s alum and retail veteran to get a first-hand account of what it takes to outlive trends, develop taste, and reflect on their latest East Hampton pop-up.
The fashion industry is famous for its unpredictability, from economic swings to the ever-shortening trend cycles. Retail rarely sits on solid ground unlike healthcare or energy. How do you stay grounded amidst all of the external forces?
When you’re what I call a “merchant leader,” you’re dependent upon your instinct, because there’s no right or wrong answers when you try to choose an assortment of merchandise.
For example, when I went to The Gap, things took off like a rocket—beyond anything I had done before—and I just kept trying to do better. The global stock market crashed in 1987 and the stock went with it, so the volatility comes with the job even if you’re doing everything right.
I watched Steve Jobs get taken out of life at such an early age, but he always said the same thing when he was still alive, and that’s part of why I admired him so much. Push through the critics, be smart, and be a detective. I’m addicted to crime stories and the great detectives. They take a sample of DNA, and then it leads to the next clue and the one after that.
I think business is the same way. I see a clue and follow it until the end game. People think dealing with it isn’t that important. And I say, “everything a customer sees is important—I live as a customer.”
How do you balance offering innovative and unique styles that appeal to the fashion-conscious East Coast shoppers while also catering to what you and I would call the “mall shoppers” who seek more familiar and accessible options?
To me, whether it’s clothes, cars, or even art—they should never go out of style. Andy Spade [husband of the late Kate Spade] worked with us, and he had some great quotes—”You can have anything you want if it can be bought, but you can’t buy style”—fantastic.
We’re not a trend follower, nor are we in the high-fashion business. Good looking clothes resonate with everybody and that’s what we’re after. I try to look around corners and sometimes I make a mistake, but I look at my feelings and those around me for insight. You have to have people on your team that, if you know, you know, and if they get it, they get it. And that’s who I lean on.
Alex Mill just opened an East Hampton pop-up this summer. And while it’s temporary, all three of the Alex Mill flagships haven’t ventured beyond New York. What was the motivation behind choosing a New York beach town instead of treading uncharted territory like LA, West Palm Beach, or even Boston?
The location came up, and I happened to know the landlord, Paul McCartney’s brother-in-law Jay Eastman. We shared some back-and-forth, and by the next day, he and I had a handshake. I took a little risk. Some people thought it was a big risk, but I said to Jay that “I don’t care if we make a nickel, I just don’t want to lose money.” And he accommodated the deal, and we killed it out there. But why East Hampton in the first place? You simply cannot buy a better fashion audience in the world than in the Hamptons.
I loved the first glimpse of Alex Mill’s fall collection, especially the use of camo and venturing into formal suiting. Is there anything unexpected that Somsack’s team is working on for the following FW24 deliveries?
What we’re doing is we are doing a lot of scarce collections—we call it small-batch. Alex Mill will be collaborating with Schostal—a 150-year-old nightwear brand out of Rome—coveted among their loyal shoppers. The campaign will also feature a familiar face we’re thrilled to work with. Why am I excited about it? Because it’s scarce, famous, and beautifully done—it’s amazing.
What advice do you have for men who want to look their best?
Never buy something when there’s a reason not to. Here’s an instance of that—I got invited to the Ford Motor Company design headquarters years ago. I thought, they’re in the design business, why do they care what I think? The chairmen showed me these new Mustangs, updates of the great, old, classic cars Mustangs are. He asked me with 100 or so CEOs in the room “Mickey, what do you think of this car?” I said, “I love classic Mustangs, but I will never buy that car because the wheels are ugly.” There’s seven people designing these vehicles—the wheels, the grill, the hood—as the saying goes “a camel is a horse designed by a committee”.
So I would say the following: taste and style are the prerequisites. You can’t go wrong this way, whether it be automobiles or khaki pants. So continue to develop your own way of dress, and taste will naturally come along with that process.
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Khakis never go out of style. Congratulations to the Chino.