Jenna Lyons

For Jenna Lyons, one of the rewards of a 27-year career at J. Crew is crystal clear on Halloween when a lot of young girls and guys dress like her.

“That is really cool. That’s really fun,” she said, nearing the end of a 90-minute talk at the Fashion for All Foundation in Brooklyn.

About 25 students and industry newbies heard about the highs and lows of Lyons’ work life — and a bit about her personal life — Thursday night. Nearly two years after exiting the J. Crew Group as president and creative director, the California-born creative discussed her plans for a reality TV show, an aversion to social media, the creative freedom found outside the c-suite life and partying in the White House with the Obamas. Before delving into her trajectory, Lyons apologized in advance for the swearing that would follow. It did.

Wearing a tuxedo jacket, white shirt, camouflage pants, striped socks and well-worn white Converse All-Stars, she discussed her contrasting tendencies and more self-conscious early years. Having conical teeth, huge bald spots and scars “pretty much all over” due to a rare genetic disorder made connecting with her middle school classmates challenging, since they often felt awkward around her, she said. “So I was kind of a loner.” In these social media-minded days, she told the crowd, “There is always going to be someone with more Instagram followers. Full transparency — it’s one of the reasons I have been afraid to do it. I am still at the end of the day that girl in sixth or seventh grade, who felt not great about themselves. I’m scared to put myself out there and be like, ‘I didn’t get so many likes. Nobody liked my pictures.’ It’s hard. I don’t want that level of scrutiny. I don’t think it’s great for my psyche.”

Taking a mandatory home ec class, which entailed learning to balance a checkbook (“still can’t do it”), bake and sew, being tall and gawkily skinny, she started making her own clothes. “Growing up relatively poor” on her mother’s piano teacher salary — her father had left years before — “we lived in a neighborhood that was relatively wealthy but we were kind of swinging it,” she said. Recalling how she envied two “cute, big-boobed, big-haired” twin sisters who got twin Maseratis for their 16th birthday. When one of them slipped her a note in social studies class that read, “I love your skirt. Where did you get it?” Lyons said a lightbulb went off because she had made it. After Lyons’ grandmother gave her a Vogue subscription and a sewing machine for Christmas, she started making clothes for herself and friends. Being able “to change the way people saw me and change the way I felt was really special to me,” she said.

Interning at Donna Karan in the late Eighties, Lyons was puzzled by the $2,000 price tags, knowing that was out of reach for herself and everyone she knew. A job offer fell flat because the scant salary would have been comparable to “working for free,” so she went home for the summer to waitress and regroup. Fast fashion had not been born, but J. Crew was striving for aspirational, shooting models such as Christy Turlington and Linda Evangelista in sweatshirts. “They were trying to make something beautiful for people who didn’t have millions of dollars. That’s why I went to work at J. Crew because I wanted to make anyone feel that they were beautiful, and not just people who had lots of money and were stick-skinny.”

In the number-two slot at J. Crew, Lyons oversaw three brands — J. Crew, Madewell and Factory — with 680 people reporting to her. “It sucks your creativity. With this new thing that I’m starting up, I’ve realized the last thing I want to do is to manage a team of people. Managing people is probably one of the most difficult things that I’ve had to learn and you don’t really learn it in school,” Lyons said. “The biggest mistake I made was packing my days so full to get everything done, answer all the questions and everybody else’s questions that I didn’t leave time for myself to just think about things, to look at magazines and art books, to take a break. I couldn’t get myself out of the office to go to an art gallery, and on the weekends, I was with my kid and he didn’t really want to go to that stuff.”

Free from the grind of full-time work, she has changed that, noting that she has seen the Hilma af Klint exhibition at the Guggenheim three times. Magazine features about her homes far outpace ones about her career, but Lyons plans to put those decor skills to use with her new TV show. “We start filming in February or March. This time I’m not going to be designing which is great…I’ll be curating fashion, home and beauty on a pretty big scale. I have a lot of work to do. I have no team [yet]…” Lyons said, confirming she has full creative power for the yet-to-be-named show. “AT&T purchased Time Warner Media, which is HBO and all of the shows that are on there so it will be on that channel and there will be a digital component. It won’t launch probably until November.”

Lyons spoke openly about how after she and her husband divorced years ago, she started dating a woman and the media descended outside her home. “Because I had my son in the press before [in a J. Crew ad] the way it works legally is the press has access to your kid. You can’t ask them to not shoot your kid. I had photographers outside my building, trailing me while taking my son to school and waiting outside.”

From then on, she decided to steer him from the media so the 12-year-old will not be in the show even though he is dying to be on TV. “I don’t want him to ever be in my stuff. Who knows what’s going to happen? I’m sure there will be something that will go wrong on the show. I’ll say something or get somebody in trouble, or somebody will be mad or people will just want to start following him. It’s not worth it for me to include him. If he wants to do something later…”

At J. Crew, she committed to shepherding the brand in the best possible way, and said she understood the business and the importance of maintaining the brand’s integrity and its connection to customers. The aim was to get it to the next level, “It wasn’t Jenna Crew. It was J. Crew,” she said. Lyons emphasized the importance of teamwork, advising the students and aspiring designers several times to “we” instead of “me.”

Recalling how Michelle Obama’s stylist [Meredith Koop] contacted J. Crew a few months before the 2013 inauguration looking for sketches for the First Lady and her daughters Sasha and Malia. “We said, ‘Absolutely. Of course.’ We sent tons of sketches, fabric swatches but the turnaround time was insane and they wouldn’t give us measurements,” Lyons said, explaining that, as a global company, the typical turnaround time was seven months or best-case scenario three months for a sample. After multiple sketches were OK’d, Lyons’ team started making “all these clothes” after finding local facilities. “I couldn’t tell my boss, Mickey Drexler, because he is the biggest chatterbox [laughs good-naturedly] and we were sworn to secrecy [to keep the secret safe.] I told the head of finance, who I worked with closely, obviously, I’m going to spend $150,000 in the next three months and you can’t say a word about it. I had to pay people to do stuff in New York because we don’t have factories in the U.S.”

In the end, Obama chose an Isabel Toledo ensemble but the girls wore J. Crew head-to-toe. Over time, Lyons’ team fulfilled other wardrobe requests. “Anything they asked us to do we would bend over backward,” she said, adding that the stylist later invited Lyons to various White House parties including birthday ones for the First Lady and the President. “It was not what you would think. It was not star-studded. It was really just the people who had helped them and done things with them that helped them to get to where they were,” she said. “When Stevie Wonder came out and started to sing [at one party], I was standing next to Michelle and I started to bawl. Bawl. She said, ‘I saw that.’ I said, ‘Can I hug you?’ and she said ‘Yes.’ I felt like I was holding on for a little too long.”

Lyons doled out lots of career advice. “If you find yourself talking about yourself, stop talking. Just shut up. People talk a lot about themselves,” she said. “If you are worried about being promoted and how you’re going to get to the next level, you’re focused on the wrong thing. If you are worried about making beautiful product and working with amazing people, you will have a great time and chances are you will be successful….It’s not really just about you. You’re just a piece in the pie. None of you, not me, can be successful on your own. I know a lot about Kim Kardashian’s business and the people she relies on, the team she works with. Yes, she’s that focused but if she didn’t rely so heavily on a few key people and she is very good to them.”

Lyons is skeptical about social media. She told students that Instagram is a tool, not a foundation to building a business. As for her own social media, she said, “It’s baaaad. I don’t have one. When Instagram and all that started, my life was getting a little crazy. I was just starting to date a woman [Courtney Crangi]. I was in the press a lot and that wasn’t a good situation for me. I decided it wasn’t the right time for me to go out and have a presence and I also didn’t know how to do it. I was already established in my life and my career, and J. Crew had its own Instagram, so did Madewell,” she said. “Now I’m faced with figuring out what I’m going to do. In a three-hour meeting with these people who are building the web site for the show, they said, ‘You’re going to have to get into the game.’ Any time I have been real about my imperfections or faults that has been far more interesting. This world where people are presenting this perfect version of themselves is really not that exciting and not that authentic.”

Dismissing the suggestions that everybody loves her, Lyons said, “That is not true. I have an ex-husband and an ex-girlfriend who would disagree and probably my mother.”