“OK, what gelato?”
“Chocolate, vanilla” – Drexler has a “you see” smile on his face – “Then today we have Orange Allspice as a special.” This stops Drexler. It is clear that he thinks the Orange Allspice was someone’s not very good idea and that a lot of it is going to be left in the restaurant’s freezer at the end of the day.
“The meatballs are very tasty,” he says to comfort the waiter, who looks a little confused about his role here.
“You should try them on the pizza!” says the waiter helpfully. Drexler looks at him. “But you have meatball pizza, right?” he says carefully.
“Yes!” says the waiter, clearly not getting the point: if Drexler wanted his meatballs on his pizza, he would have ordered them that way. He didn’t, partly because he doesn’t believe in confusing things: food or fashion, you need to be clear about what you stand for.
Personally, he has always been very clear about where he stands and it did, indeed, begin with that Bloomingdale’s job: value for money. When he joined J. Crew as chief executive in 2003 (he didn’t reach this in his career speech but he had been fired from Gap six months earlier after a very bad 2001-02 when the brand seemed to have lost its way), it was “a discount business. But I thought it had a great name and good real estate, two things I had also seen in the Gap, and could be taken to another level ... At the time, there was a lot of white space in the market between very cheap clothes and designer.”
In the space, Drexler saw opportunity. He installed the loudspeaker system because, he says, “I couldn’t waste a second; I couldn’t be waiting for people to call me back,” and started redefining the brand as understandable, good quality clothes with a fashion edge. He gave significant power to designer Jenna Lyons, who had previously been buried in the women’s creative team, and last month they held their first presentation during New York fashion week; Ikram Goldman, owner of an influential Chicago boutique (and the woman who dressed Michelle Obama and her children in J. Crew) said it was “the freshest thing” she had seen.
The waiter takes the plates and asks if we want coffee. We do, and Drexler asks if they have any biscotti. “The plate comes with four: two chocolate and two vanilla,” says the waiter. “I don’t want chocolate,” says Drexler. “Can we just have the normal kind?”
He gets what he wants, as he often does, but not always. Which brings me back to the question of his biggest mistake and the emails and phone calls that followed our lunch. While we were eating, Drexler had told me that he tried not to work on the weekends but that he did think. After our lunch he had been thinking about the mistake question and reading the news about Gap closing stores in America to expand in China. That had made him realise what his mistake was. So, though he was in California, he called to tell me. The mistake happened when he was at Gap and the brand was undergoing a “rapid expansion”, increasing its real estate holdings by almost 70 per cent, a move he opposed but ultimately oversaw. Now he says, “I didn’t fight the board hard enough to stop it. I should have fought harder.” He isn’t blaming them for a bad decision; he’s blaming himself for caving in.
Later, I email him: “Have you made that mistake again?” and a few minutes later my phone rings. “Not so far,” says Drexler, who knows he no longer needs an introduction. “Hopefully not ever.” He pauses. Then he says cheerfully: “Call me back if you think of anything else you want to know!”