Jenna Lyons on Continual Reinvention and Why She’ll Never Start Her Own Fashion Brand

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Jenna Lyons made her name during 20-plus memorable years at J.Crew where she eventually became president and executive creative director, but her second act has been just as fun to watch. Between TV gigs, consulting, and just being the coolest person in every room, it’s time to check in with this beloved fashion fixture.

What are you up to these days?

After leaving J.Crew, I spent time consulting with Jonny Bauer’s team inside Blackstone. I focused primarily on value creative projects related to real estate, home, and fashion. I was excited about the opportunity to do the actual work as opposed to managing a massive team. I enjoyed the visibility across categories and seeing trends evolving in real time. After two years, Jonny decided to carve out a team and start his own company. He asked if I would join him, to which I quickly replied yes. My previous experience at J.Crew Group, as well as sitting on the board of Shake Shack for 10 years, has informed my thinking around the work I’m doing now. Our focus is giving a brand a set of organizing ideas that become the filter for every decision—brand strategy that focuses on value creation.

J.Crew is where you spent a lot of your career and made your name. What are your fondest memories from your time there?

There’s nothing more powerful than your heroes or the people you look up to coming to celebrate your work. I remember distinctly when I asked Solange [Knowles] if she wanted to come to our show [at Lincoln Center] and she said, “Can I bring my sister?” I said, “How many sisters do you have? Do you mean Beyoncé?” and she said, “Yes,” and she asked if they could wear something. I didn’t have any experience in that world of dressing celebrities. We had never really done that. Truthfully, I didn’t know how it worked. We sent her one dress. It was that moment you realize you’re being recognized as a team on a much bigger level. It was so rewarding, and we were so excited. She was a hero of mine. And of course, the Obamas wearing our clothes and having an opportunity to go to the White House and share in that moment was just otherworldly. I still can’t believe it. Because there were no cameras at those events; a lot of people don’t know about it. I went to Michelle Obama’s 50th birthday party and got to watch Prince sing four feet away from me, and Stevie Wonder sing with tears running down my face. I couldn’t believe I was there. To hear Stevie Wonder sing, not through a microphone, but to hear his voice standing in that room. It gives me chills just thinking about it. It was incredible. There’s those moments, and then there’s the simple moments. I remember standing in an airport in London and seeing our clothes on people. That was special.

President Barack Obama and first lady Michelle Obama (in J.Crew) walk in the Inaugural Parade on January 20, 2009 in Washington, DC. (Getty Images)

Do you think someone could have the longevity you had at J.Crew today?

The way it happened for me, exactly, probably not. That was a specific point in time and life and the world. We’re seeing some incredible trajectories of brands that are breakout and in the zeitgeist. I know a lot of people have a lot to say about Kim Kardashian, but what she’s done with Skims is pretty remarkable. Aimé Leon Dore has completely exploded. It’s pretty impressive. That didn’t exist 10 years ago, and they did it on their own. I did it inside of a company. I think it’s absolutely possible, but the way you play the game is different. The way you execute it would be different, but it’s 100 percent possible.

What were you like growing up? Were you the cool girl in high school?

I have a genetic disorder that affects my skin, my teeth, and my hair. When I was younger, I had chronic yellow teeth because they were shaped like cones, and I had big bald spots in the back of my head and I have scars everywhere. I was teased mercilessly. My mom was a piano teacher and didn’t know anything about fashion or care about clothing. It was not part of my lexicon. I was definitely an outcast, for sure. I remember in seventh grade, I took a home ec class, and I learned how to sew. I was shopping in the big-and-tall section because I was so tall, and I made a bias-cut skirt and it fit me perfectly. It was the first time I had anything that really fit me. One of the popular girls in school sent me a note in social studies asking where I got my skirt. And it was the first time I had positive reinforcement, and it was something that I had made. It made me feel so good that someone liked something I was wearing, and I felt good about the way I looked. It was one of those moments that was really powerful. My grandmother gave me a sewing machine for Christmas, and I got a subscription to Vogue and that was it. I was hooked. I was not the cool girl by any stretch of the imagination.

You came to New York at 18. What were you like back then?

I was so naive. I came in 1987, and I remember so specifically that I had never met a gay man before. I came from a small suburb of L.A. There were no out gay men. I certainly never met a gay woman before. I remember my first day at Parsons, I met this guy and I thought he was the most fabulous person I had ever met. He was so outspoken and would make comments about what people wore, good or bad. He took me to the pier, and I watched men having sex on the pier. And he took me to Nell’s, which was a crazy club. This was pre-Giuliani. He changed New York so much and made it more sterile. It felt gritty. I saw Paris Is Burning and started going to drag shows. We would go to Florent at 3 in the morning after staying out all night and go to school the next day. It was so fun and crazy. I was literally a deer in the headlights.

Did Diane Keaton have a big impact on your style?

There’s quite a few women who did. What I loved about Diane Keaton was that she had a playful and relaxed approach to dressing. I was shopping in the men’s section because I couldn’t find things that fit me. She was shopping in the men’s section because she liked the way it looked. I was fascinated by this woman who embraced it, and the public embraced her and yet she still wore lipstick. She wasn’t playing a character; she was saying this is the way she likes to look. I found that charming, especially because she was so warm. I loved Diana Vreeland, too, but she was much more about a bold statement.

Michelle Obama in J.Crew

Who are some young designers on your radar today?

I love what Willy Chavarria is doing. I think he’s created such an amazing world. It doesn’t feel like anything else. It feels completely his. You really feel like Willy Chavarria’s world is his own. He’s been at it for awhile, but I love how he’s being embraced. The clothes hold up. I really love Petar Petrov. He’s not American. I wear a lot of his clothes. I love Husbands Paris. I send every man I know there. [Nicolas Gabard] has a strong narrative and has created his own world. I love what the girls at Matteau are doing. I love Kallmeyer.

Why haven’t you started your own brand?

Oh, God. Because it’s so hard. I was on the CFDA/ Vogue Fashion Fund committee, and I saw how hard it was. If you don’t have a big company behind you, it’s very challenging. I had already worked really, really hard. I was exhausted. Having your own line is 24/7. I had already put my blood and tears into J.Crew and I needed a break. When I took the break, other things happened, like I started doing TV. It never really presented itself. I would be more excited to take on Ralph Lauren or something that has a preexisting road map and continue it. I think it’s something I would have done when I was younger.

You’re on podcasts a lot as a guest. Why haven’t you done your own yet?

I felt like everyone was jumping on the bandwagon. I was going to do one at one point, but then they started asking me this, this, and this and I thought, “Okay, you need me to do all of that?” I was juggling so many things and had too many irons in the fire. To do podcasts well is actually a big job. I didn’t realize how much output that would take. To do something well, you need to put time to it. The ones that I like the most are when there are two people, when there’s a cohort. If that were to come up, maybe!

The Real Housewives of New York City is back this month, and you’re not on it this season. How do you feel about that experience in retrospect?

I’m happy I did it and happy I understand what that engine is about, and it demystified it quite a bit. There are a lot of misconceptions about how it’s done and what it means. I feel a lot of clarity around it. I feel good that I didn’t do this season. I saw the trailer and I thought this is probably what it needs to be, but it’s not the right thing for me. I’ll be a viewer, and that’s fine. I spent 27 years in one job and did everything that everyone expected of me from getting married, having a baby, buying a house, and all these things. I was always concerned that I was representing the brand in public. I remember distinctly at one point I was thrown in a pool at a party and I got called into HR [at J.Crew] and they said I represent the brand, I can’t be thrown in a pool. I was like, “I didn’t throw myself in the pool, but noted.” It was the first time in my life when I didn’t have to answer to anyone so I thought, “Why not?” about doing the show. I have no regrets, but it was f**king weird.

What are your passions these days?

I still love interior design. I’m trying to not do as much as I used to do. I used to have a full dance card. I’ve been trying to spend more time on the water. We have a little boat, and that’s my absolute happy place. That’s been so nice to spend less time doing and more time ideating and thinking.

Solange Knowles, Jenna Lyons, and Beyonce Knowles in 2012 (Getty Images for Mercedes-Benz Fashion Week)

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