He visits every office, store and distribution centre, and makes an effort to meet every new employee, although he's always Mickey, not Mr. Drexler. He'll notice if light bulbs are too dim, or how long the water cooler has been broken. And it's up to him to remember his cousin's birthday, although one of his assistants jots down the note once he says it aloud and she'll gently remind him later.
There have to be some perks to being in charge of a company that has steadily gained style cred since Drexler took over in 2003. It's also expanded from its signature prepster khakis and T-shirts that launched 30 years ago as a catalogue-only business to a high-design collection of casual and dressy clothes in bold colours and prints in 287 free-standing stores, including its Madewell label, and is available in 103 countries online.
Michelle Obama famously told comedian Jay Leno on his talk show during the 2008 presidential campaign that she would order J. Crew clothes online late at night.
J. Crew lands in China this fall with its first retail presence outside North America in Lane Crawford department stores.
The company even previews at the upcoming New York Fashion Week, sandwiched on the schedule between Tory Burch, Badgley Mischka and Vera Wang.
Check out the cool and colourful J.Crew ad campaign images for fall 2012.
His name means something, and he can get a reservation at any restaurant he wants, but, he says, he'll judge that hot, hip eatery by how they treat people on his staff when they call for their own table.
"I used to be not me, 'Mickey Drexler.' I was me, just regular Mickey Drexler, the rest of my life, and I remember that," he says.
It takes a little effort to keep up with Drexler, 68, who previously served as CEO of Gap Inc. and is a director at Apple. He jumps from topic to topic as if he's playing pingpong but never seems to take his eye off the ball.
He gives more than a cursory glance to an email blast about the brand's new ironless shirts for men. The pitch is good, although he personally isn't completely sold on the ironless shirt — he is, after all, in a slightly rumpled pinstripe button-down that is part of his daily uniform with dark-wash jeans and a navy single-breasted, double-vent Ludlow blazer — but, he rationalizes, it's what some customers want. And what customers want, he tries to deliver.
He's been known to personally respond to a letter from a shopper who has a problem or a suggestion. "People think it's special if we respond, but it shouldn't be that way. For us, it all starts at the store and with our customers."
It nags at him that a sales associate reported moms have complained about the scratchiness of some embellished shirts in the company's children's line.
Drexler seems to be honest and candid with his employees, sometimes resulting in criticism but more often he'll give a happy shout-out.
During a recent tour of a J. Crew store in the Union Square neighbourhood of Manhattan, not far from company headquarters, the staff isn't surprised to see him. They tell him the new bridal salon in that location is doing well, better than J. Crew bridal was doing as a stand-alone shop on Madison Avenue.
When it comes to light that the Goldsign Jenny-style skinny jeans (with a $288 price tag) are popular with shoppers, he calls the office to congratulate the denim team. "Put me on the loudspeaker," Drexler says.
He makes regular announcements at headquarters, sort of like the principal of a school. "When you say something and a thousand people are hearing it, you hope you leave an impression. I'm also sort of advertising."
He adds, "I don't know who listens and hears me, but someone is."
In reality, all the people within striking distance seem to have at least one ear trained on what Drexler is saying. In the open-space office, people respond to his questions without him even really asking.
They also keep him moving on schedule, nudging him to this meeting or that. Drexler often takes the long route there, just to pass by others' work spaces to check in on what they're working on or the daily buzz.
Having breakfast with investment bankers — like he did on this day — isn't his usual routine, but maintaining relationships with the business community is part of his job.
Later, he was breaking bread with the company's 27 corporate interns.
"I gave them all an assignment yesterday. I said, 'If they had the power to make the department they're working in better, what would they do?'" Drexler says. "And I want individual answers, not a 'group.' I want people who are looking to do things better. ... I'm an agent of change all day long, and I want to meet other people like that."
This talk about interns leads Drexler back to his management training days at Bloomingdale's. He was in the program with the son of the CEO of Macy's. Meanwhile, Drexler and his new wife — to whom he's now been married 42 years — had just bought a couch from Macy's that left them cold.
"Too big, too expensive, all wrong," Drexler describes. They tried to return it, or even exchange it, but they didn't get anywhere until Drexler tapped his relationship with the CEO's son.
Not long after that, the couch was gone, but they still had to pay a return charge, and Drexler says he still thinks about it. "Service drives a lot of my decisions," he says.
This month J. Crew relaunched its personal shopping program, renaming it Very Personal Stylist. It will be available at all stores with an emphasis on accommodation, whether that's body type, budget or time.
"I didn't like the name 'personal shopper.' That makes it sound like too much of a commodity and not personal enough," Drexler says.
He also hopes the new approach takes the sting out of asking for help. Right now, not enough people seek the expert fashion guidance they can get for free, Drexler says. Maybe it's because they think they'll be in for the hard sell or they'll end up with a look that's not really who they are, he muses, but everyone can use a second opinion and a little friendly advice.
Drexler asks a new sales associate — someone who's been on the job in the men's department for just two days — what style of jeans he should wear.
"Vintage straight," the employee answers without hesitation.
Yes, he's in the fashion industry, but he's not a fashion guy. He relates more to the hospitality business, Drexler explains, which is why he uses a lot of food metaphors and compares J. Crew to a fine restaurant or hotel more than he does other retailers.
"The No. 1 thing is the product. The goods have to be good, but I care about how you feel about it," he says, noting that he doesn't believe any advertising — not the company's new ad strategy that broke in September fashion magazines or its 40 million catalogues a year — can compare with word of mouth.
"Treat others as you want to be treated," Drexler says. "Isn't that in the Bible or something?"