At his first staff meeting, Drexler openly declared his intentions: “Everything and anything is under attack.” As Lyons recalls, Drexler asked her to show him the sample clothes that had been created for the fall 2003 line. “He was testing me,” Lyons says. “He said, ‘Don’t worry about how much money is made on each item. Tell me what you think.’ We had this sweater that looked like a poodle. I hated it but it did huge volume. I was honest. Clothes kept dropping on the floor. He had no fear.” Still, fall 2003 was mainly a bust. “We didn’t have time to redesign, so we brought back too many J.Crew icons,” Drexler says. “They were old and a little tired.” About the only bright spot was a relatively small order of colorful Loro Piana cashmere sweaters, priced at an affordable $128, most of which sold out in a month.
Drexler decided to take J.Crew upscale—without abandoning the company’s preppy-basics heritage. The idea was to appeal to the customer who has graduated from the Gap but wants something hipper, and less expensive, than Ralph Lauren. Drexler also decided to improve the quality of the clothes to impart a greater sense of value, and to imbue the brand with a more fun sensibility. “I look at companies as price-players or quality-players,” Drexler says. “The only way to go with J.Crew was quality.” He immediately banned the company name from its garments, in the belief that upscale shoppers are tired of being walking brand advertisements. He nixed the signature “oar” logo. Instead, he pushed the designers to come up with a new conceit, and they brought back an old J.Crew favorite, “critters”—whimsical preppy symbols such as lobsters, mermaids, and martini glasses. Drexler emphasized catchy details, such as linings and trims, to freshen familiar styles. “A detail can make you buy something,” Lyons says. “When you have a cardigan, it’s a cardigan, but if it has a big pink grosgrain ribbon on the inside placket, and diamante buttons, it makes people think, I need another one of those.” He switched manufacturers, too, using some of the same high-end factories used by Prada, Coach, and Oscar de la Renta.
Drexler has looked at tens of thousands of garments in his career, searching for the winning look, editing out the items that don’t work, and suggesting changes that can turn an otherwise blah shirt into a best-seller. Ask him how he senses, six months to a year ahead, what people will want, and he throws up his hands. “I don’t know,” he says. “I have a thing. I don’t remember if I figured it out or it was always there—an instinct.” There are clues. He’s an insatiable window-shopper who has no qualms about walking into stores and quizzing strangers, both clerks and customers, about their likes and dislikes. He credits his wife of 35 years, Peggy, for insights into how people behave, frequently prefacing comments by saying, “When you’re married to a psychologist . . . ” Drexler pays close attention to the fashion instincts of his children, a son, 26, who works in advertising, and a daughter, 12. He also seems to have a physiological gift, not unlike, say, a Derek Jeter. Last summer, an eye doctor told Drexler that he had never seen a patient respond so rapidly to external movement and stimuli. “I spot detail quickly,” Drexler says.
For this fall, Drexler invested heavily in high-end merchandise, including $500 men’s cashmere blazers (more than double the highest price for a jacket in the 2002 catalogue), a $395 lacy gold dress, a vastly expanded line of shoes, and accessories like belts made of rep-tie fabric. To generate buzz, he commissioned the equivalent of a couture line: small quantities of a few specialty items, such as a $1,500 white cashmere toggle coat. Just as he did at the Gap, Drexler is giving the J.Crew stores a makeover. The dark-brown walls have been painted a soothing latte color and a vibrant green, even the music soundtrack has been changed from bland instrumentals to an eight-hour mix including the Rolling Stones and Elton John. When customers say, “I love that song,” the idea is, they stay in the store longer.
Drexler has also been retooling the staff. Of the 400-plus people at J.Crew headquarters when Drexler came onboard, more than 100 are now gone—some were fired, others read the handwriting on the wall. So far, more than two dozen of their replacements have come from the Gap. The brain drain includes Gap senior V.P. Tracy Gardner, now in charge of merchandise buying, Old Navy menswear designer Todd Snyder, Old Navy visual stylist John Valdivia, and the Gap’s head of personnel and head of store operations. “This is not about revenge,” Drexler insists. “It’s about hiring the team.” Drexler’s most important hire has been Jeff Pfeifle, whom he wooed from Old Navy to become J.Crew’s president. Where Drexler is a big personality with an over-the-top style, Pfeifle is a calm delegator with a dry wit. If it seems that Drexler is attempting to avoid the management mistakes of his past, he is. “In this job,” he says, “I’m applying everything I’ve learned—and everything I’ve fucked up—in my career.”
Sitting on the deck of his Martha’s Vineyard retreat, Drexler looks out at the late-morning mist rising off his own private stretch of the Atlantic. The home is a handsome shingled beach house with a retro fifties look: The living room is designed to resemble a ship’s prow with a wooden ceiling, and vintage-looking fabrics cover the furniture. A pair of green Wellington boots accidentally left outdoors has faded from the saltwater breeze. Most people would be annoyed by the mishap; Drexler is thrilled by the new sea-green color, planning to bring the boots to the office to duplicate the shade. “I love to work,” he says. “I have a passion for what I do.”
It’s no surprise. Drexler was born into the fashion business, and his father, Charles, a button and piece-goods buyer, had him work weekends ticketing garments and taking inventory. Work must have been a relief from a difficult childhood; his mother, Mary, was diagnosed with breast cancer when he was 2, and died fourteen years later. “She was always sick,” Drexler says. “In those days, cancer was a hush-hush thing. She had a hard time.” Like many kids of immigrant Jewish heritage, Drexler was highly driven. He grew up in a one-bedroom apartment on Barnes Avenue in the Bronx, attended Bronx Science, spent two years at City College, transferred to the University of Buffalo, and went for an M.B.A. at Boston University, where he met Peggy.
In 1967, Drexler landed a summer job at an Abraham & Straus store in Brooklyn, on the sales floor, not in the back room. “I loved the fact that if you put goods on the floor,” he says, “you could watch them sell.” But after stints at Bloomingdale’s, Macy’s, and A&S, Drexler became frustrated with the department-store business: If one store cut prices on swimsuits, “we all marked our merchandise down.” Instead, he became intrigued with the Brooks Brothers model—the store sold only its own exclusive merchandise and was less vulnerable to price wars. “Brooks Brothers was my awakening,” he says. He also had a personal revelation: “The nice clothes were all designer names,” he says, but on a middle manager’s salary, “Peggy and I couldn’t afford it.”