At 43 years old, Lyons has split her life almost evenly between New York, where she moved in 1987 to attend Parsons, and Palos Verdes, California, where she grew up. Adolescence was the iffy experience you’d expect for a beanpole with a severe cutaneous condition. Two good things, however, happened in seventh grade: Lyons took a home-economics class and learned to sew, and her grandmother gave her a subscription to Vogue. The first issue that arrived, in 1982, featured a blushing Isabella Rossellini on the cover and an Issey Miyake spread inside. It did not take Lyons long to memorize every price, designer’s name, stylist, and model in the magazine. “I knew mastheads. I would read them cover to cover, and then I would go back and read them again. They were dog-eared,” she says. Squishes of face cream, Borghese lipsticks, tweedy clothes that must have weighed a hundred pounds: The ads and editorials of those first Vogues are catalogued neatly in Lyons’s mind, and less neatly in leaning towers around her office.
It was during this period that Lyons sewed her first piece of clothing, a yellow rayon skirt printed with jumbo watermelons. Long, liquid, and cut on the bias, with an elastic waistband and a hand-stitched hem, the skirt turned out to be an epochal piece of rayon. It fit the preteen’s Gumby proportions, it wasn’t from the big-and-tall section of the store, and the coolest girl in school, Dana Peterson, told Lyons that she liked it. “When I put the skirt on, I looked like a totally different person,” she remembers. By the time she got to high school, Lyons was sewing with whatever she could scrounge up from the fabric store in Palos Verdes: calicos in ditzy florals, quilting fabrics. When she moved to New York in the late eighties, the spoils of the city had a talismanic effect. A four-ply silk crêpe at B&J Fabrics, Lyons says, almost brought her to her knees.
“I can’t tell you the amount of women for whom Jenna invariably comes up in conversation.”
J.Crew was a small company in 1990, when Lyons went in for an interview. The brand styled itself as an energetic all-American label that was neither Talbots nor Ralph Lauren nor L.L. Bean. “J.Crew was the life that you could have,” Lyons says. “It was about hanging out. There was no price of entry. You might have a house in Maine on the beach, but you didn’t have a yacht and twelve horses.” For a brand that specialized in unisex wardrobe essentials, it also managed to be slightly hip: People like Ingrid Sischy wore J.Crew, and the company advertised in Spy magazine.
There was no job for Lyons when she interviewed, but the head of recruiting made an unusual request: “She asked if she could have Xeroxes of my portfolio, which is kind of unorthodox,” Lyons says. “But I trusted her.” In the meantime, she moved back home, donned a white polyester polo shirt, and went to work as a waitress. At the end of the summer, J.Crew called Lyons back to New York to meet with someone in men’s knits. She auditioned with a set of eight sketches that were FedExed to Emily Woods, J.Crew’s co-founder, in California. Woods, enthused by the sketches, requested that Lyons fly back and meet with her at home, where she offered the young graduate a job on the spot. Lyons accepted without asking what her salary would be.
By the early 2000s, the brand had foundered. Boxy acrylic cardigans shared catalogue space with poly-cotton sleepwear and chinos lined in flannel. There were stretch velvet pants and sueded football jerseys, and zip-cardigans in a pattern that looked like bathroom tile. Four CEOs had cycled through in five years. The company’s credit rating was cut, profits faded, and morale was low enough that Lyons can only describe the time in battle metaphors. “We were lost soldiers—working away, following orders,” she says. “I was shell-shocked and burned from what was going on. Fried.” There was the prevailing sense, internally, that things could not possibly get worse.
On a Sunday night in January 2003, Lyons received a call from the company’s then-CEO explaining that he was out and Mickey Drexler would be in charge of J.Crew starting at eight the following morning. “I spent the whole night online reading about Mickey and having a panic attack,” Lyons remembers. On Monday, the new boss corralled his team and informed them that they would all, in effect, be interviewing for their jobs. He did not mince words. Stores would be redesigned, old inventory disposed of. Within three months, all but two executives had been fired.
“Mickey was the best thing since sliced bread,” Lyons says. “I loved him from the minute he walked in the door.” It went both ways. Drexler intuited her coolness, asked diagnostic questions, attended closely to the answers, and figured out what the action was. “There’s a certain antenna you develop in evaluating people,” Drexler says. “Especially in an urgent environment. And with Jenna, I felt it, I saw how she thought, I saw the aesthetic. It’s a gut instinct.” Drexler allowed Lyons to prune the line, snipping away offensive but lucrative items: a hairy poodle sweater, a stretch chino, a “weird, drapey” cardigan. In place of those garments, Lyons brought in trim, tailored jackets in Italian wool and design collaborations with high-fashion names like Prabal Gurung and Dana Lorenz.