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. Drexler has been described as a micromanager and 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. In this conversation, Drexler shared insights into Black Friday sales, his experiences at Gap, working with Steve Jobs, and his opinions on good stores and sustainability.
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.
