February 15, 2018
Nine months after leaving J. Crew, former executive creative director Jenna Lyons sat down with us for an intimate conversation about reinvention. From her formative years in Southern California to her massively influential, 26-year-long career at J. Crew, she’s no stranger to the concept. But “what’s next” is a difficult question, especially now. We invited her to the Chandelier Penthouse to tell us about her journey.
Alexandre Stipanovich: When did you first experience the power of reinvention?
Jenna Lyons: I grew up in Southern California, where I spent all of my time just trying to fit in. I remember I took a sewing class, and I made this skirt that actually fit me. I didn't know that I was actually an okay size, because nothing had ever fit me in a regular store. I was constantly going to the big and tall section. I made this skirt with watermelons on it and wore it to school. One of the popular girls leaned over to me in social studies and said, "Where is your skirt from?" I was like, "I made it." I remember it was the first time I'd had any positive attention about the way I looked. It was really meaningful to me. On top of that, I enjoyed making it. It was pretty magical. It made me realize that clothes, while people think they are frivolous, can actually be somewhat transformative.
And that was also in thanks to your grandmother.
That Christmas, my grandmother sent me a subscription to Vogue and a sewing machine. I remember poring through the pages. This was back when Vogue was a different magazine. Things were very experimental back then. There were no rules, it was the wild, wild west. Issey Miyake was inside with women with black bands across their face and huge gowns, things I'd never seen before. Norma Kamali and YSL... it was breathtaking, the clothes that were in there.
Then a few years later, you moved to New York. Which is a great city to reinvent yourself in.
I got into Parsons, came to New York, and then I met my first gay man, which was really amazing. He used to work at Macy’s and one day, took me to the makeup counter there and had one of his friends make me up. I remember looking at myself in the mirror afterwards like, "Whoa. Who's that?" I was walking down the street and people looked at me in a way that I'd never been looked at before. Even in California, even though I felt better about myself in California, I was not attractive. In New York, somehow...
And then a guy looking at you on the street had a car accident.
Yeah, we were coming across the street and I was wearing a tiny little black dress, high heels, had all of my makeup done, and this guy drove past and got in a car accident when he saw me. I know that's an awful thing to say, but it was pretty transformative for me. No one had ever looked at me before. And then, someone was so busy looking at me that they forgot that they were driving a car.
What was J. Crew like when you first started in 1990?
J. Crew was a unique place back then. I was on a design team of about 13. I couldn't have the experience I had this time around. It didn't exist. The company was tiny, and so I had the experience of working for a tiny mom-and-pop company that then went public. I was sitting in the room when we were having earnings calls, and for someone like me, I never in a million years expected it. The fact that I actually made it to the board room... I still think people are going to kick me out and be like, "Get the fuck out." They didn't.
I think it's funny because so often now I see young people who have goals and who want to cross all these milestones. I think sometimes you get into trouble when you have those expectations of what you're going to do and what you can accomplish. If I had had those goals in my life, I never would have even tried. I didn't think any of that would happen. I feel incredibly blessed and lucky. I must have been somewhat good at it, but not as good as what happened to me.
When did things start changing for you?
I worked there, toiled away, and no one cared what I did, not for a long time. Then Mickey [Drexler] joined. He's a pretty magical human. He has the most insane passion and excitement for what he does. I've never met anyone who was more exhausting. The first meeting I ever had with him, he made us line everything up in the room and he was asking the merchants to go through the product and talk about what was on the line. I remember at one point, he asked whoever was talking to sit down and asked if I would go through it.
This was a room probably as packed as this one with my peers - people who were my team - and I had to comment on the product that was on the wall. And I hated the product. I thought we were going in a terrible direction and I wanted out so bad. I was like, this might be my out. And I literally just went through the room and just trashed everything.
Every time I would hold up something, he'd say, "Throw it on the floor." By the time I got to the end of the room, there were literally like seven things still hanging on the wall, and he said, "Okay. Now fill it with things you think are right." From then on, he asked me to fill in. I pulled my team together, we worked like dogs, and we found different ideas and started to replay everything that we loved from J. Crew. When we introduced them, that was the beginning of things changing. Probably six years after that, I got the big job and became creative director.
What was one of the biggest lessons you learned?
I had the most vicious fight with the CFO. I remember when I first started doing the stores, I wanted to install a Serge Mouille light in one of the stores, and it was $7,000. He said, "Listen, I just redid my house. I did all of my lights for $300." I was like, "I don’t want to see your fucking house. I don't care." It wasn't relevant, what are you talking about? I realized it was my job to make him understand, to make him appreciate what I appreciated, and also understand where we weren’t connecting. It took a lot more work for me to do that than it did to create the product. That became one of the most paramount things that I learned. You can be creative as hell, but if no one knows what you're doing or why you're doing it, it's not going anywhere.
Why do you think you poured so much of yourself into that brand?
I don't know if I've ever really thought about it. I think that's when you're in the right place, when you're not looking at your watch and wondering about when the day's going to be done or worried about when a project is going to be over, then you're in the right place. I always felt at home at the company. That's part of the reason why I don't have a home anymore.
Why did you decide to leave the company?
There was a time when, not just myself, but everyone internally, realized that we needed to change. We had little walls in the office that only came up so high, and we could hear a meeting happening on the other side. I remember distinctly hearing someone say, "We can't show her that. She's never going to go for it." I thought, wow. That's probably true. That person probably knows me. I've worked with that person for 15+ years and they're editing their work before it gets to me.
When you're ready to change, that's not a good scenario. It doesn't mean that they did anything wrong. They were doing their job and built this semiotic relationship where we were able to get a lot done. That works really well when you're running three brands. I needed that level of quick thinking on my behalf, because I didn't have time to meet with everyone to the level of detail that it would've required in order to do Madewell, J. Crew, and Factory.
But that was a turning point for me in realizing that I should help foster the change - and that fostering it meant me not being there. That's a hard thing to accept, but it became clear to me. Leaving very amicably with love and support of Mickey and the board, I decided that it was time.
How has it been making this transition?
I don't know. I've crashed. I had a horrible summer. I thought it was going to be amazing. I lived in a summer house. I was like, "This is going to be amazing," and it sucked so bad. I remember saying to people, "I'm okay," and I wasn't okay. I had a whole office full of brilliant, talented, funny, and creative people. I got to cherry-pick from amazing work and minds and have great conversations.
I knew everything that was going on because I was in this incredible incubator of excited, creative people just like me. And then all of a sudden, they were all gone. It was just me in my apartment. I've always known what I wanted and where I was going. This is the first time in my life that I don't. I've been really fortunate to have time to figure that out. It feels like the possibilities are endless, and I don't feel the responsibility to take another job tomorrow.
What’s inspiring you right now?
I just listened to this podcast. It was about an experiment where they took two groups of people and put them in different rooms. Each group had the same set of boxes. In one group, they had access to the Internet, access to a library of creative books, anything they wanted to see, and they had paint, tools, and all kinds of things. In the other room, all they had was a phone book. They stayed in there over the course of a couple of weeks.
At the end, when they finally saw what the people had made, the ones who only had a phone book had done some of the most creative, magical, and inspired things you’ve ever seen. They had carved the bricks, they made clay into different things, they painted and sculpted them... the people who had access to the internet and books made copies of things that already existed.
How did this inspire you?
I happened to listen to that podcast really soon after I knew I was leaving the company, and so I've purposefully stayed away from a lot. I barely read the news. I'm not taking cooking classes, I'm not taking pottery, I'm not doing anything. It's amazing. I sit on my couch, sometimes for hours, and just let my mind wander. It's really, really freeing.
We discussed how much your upbringing has affected your trajectory and way of fostering talent, in which you try to encourage the beauty and strength in everyone, no matter how weird or bizarre. What do you think is different about growing up today?
As a kid, I remember feeling like I never wanted someone else to be in my situation. Growing up today, I think one of the things that's interesting is that you can find your people in the world. I had none of that when I was growing up. The way social media allows you to deep-dive into your own experience. But there's also danger in that. You don't necessarily solicit the opinion of others. I think people who are not like you are probably the most enlightening.
Do you feel like your parenting style has been reinvented?
I think that all of my experiences have built how I am as a parent. Mostly, I revel in imperfection. I revel in messing up and appreciate it because I learned the most when I've made mistakes, not when I've been perfect. I realize having had the job I've had that people don't do better when you shame them. People don't do better when you call them out. People don't try harder when you make them feel like shit because they got it wrong. It actually is the reverse. If you can help someone through that mess and say, "Yeah, it sucked, but let's do it better the next time," or, "Let's not repeat that," that's oftentimes a better approach.
It's hard to do that as a parent. I mess up all the time, as my son will gladly tell you.
What's next for you and what are you going to do now?
I have no idea what I'm going to do. For the first time in my life, I feel okay in not knowing. I think everyone expects me to know, and I don't. You'll see.