Jenna Lyons started posting on Instagram only this year, but in many ways she was an influencer long before influencers formally existed. She was hired at J.Crew in 1990, at age twenty-one, and, in the course of her twenty-six-year tenure there, she helped elevate the company from a faltering catalogue brand of sort of preppy, sort of essential stuff to a signature American fashion company. Along the way, Lyons, now fifty-two, became a different kind of retail executive, too. Whereas most of her peers at giant clothing companies remained anonymous, Lyons became the face of the brand. In 2008—when Michelle Obama wore J.Crew on the campaign trail and name-checked the label on late-night television—Lyons remade the company’s catalogue as an editorial property featuring a new section called “Jenna’s Picks.” In these pages, consumers got a window into Lyons’s particular kind of nerdy-tomboy glam, which included anything from floral-print ballet flats to rugged leather bags and neon-colored accent belts. The premise of this endeavor was that customers didn’t want access only to J.Crew’s clothing; they wanted access to Lyons, too.
As the beloved, public-facing creative leader of J.Crew, Lyons’s personal life was on display more than the average retail executive’s. In a catalogue from 2011, she is pictured casually painting her four-year-old son’s toenails pink—an innocuous slice-of-motherhood moment that wound up becoming a subject of debate on national television. During the same year, she lit up the tabloid circuit when she left her husband for a woman. For many public figures, these sorts of news stories would represent major public-relations hiccups. But for Lyons they represented a refreshing demonstration of authenticity that made her all the more desirable to her legions of admirers.
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Of course, nothing lasts forever, particularly in fashion. By 2017, J.Crew’s sales had been tumbling for years, even as Lyons’s star continued to rise. The company was struggling to adapt to the fickle consumer appetites brought on by fast fashion and Instagram. That year, Lyons stepped down from her role at J.Crew, and tried to find her own footing. She admits it hasn’t been easy—she said that, after her departure from J.Crew, “no one was calling me.” It wasn’t until an accidental run-in with a television producer that she began thinking about a new future. The result of that run-in is “Stylish,” a show on HBO Max that toes the line between reality television and documentary. It chronicles Lyons’s sometimes messy reëmergence, following her as she launches two separate businesses: a faux-eyelash brand called Loveseen and a bigger, all-encompassing, Goop-esque life-style company. Along the way, she auditions a group of prospective employees for the new businesses. The feedback she gives them demonstrates both brutal meticulousness and a deep generosity of spirit.
Lyons and I recently spoke, over Zoom, about fresh starts, the legacy of J.Crew, and painting her son’s toenails pink. Our conversation has been edited for clarity.
At the height of your career at J.Crew, you were often described as “the woman who dresses America.” But the first episode of your new show, “Stylish,” is called “The Woman Who Dressed America”—past tense. Are you telegraphing that your days in retail fashion are behind you?
I think so. That chapter has really been written. I think that phrase carried so much weight—it felt big. I’m happy to move on.
How did you decide to get into television? Did you take the idea to HBO, or did they come to you?
It was kind of a bizarre process. I was in Los Angeles, having lunch with a friend. This guy comes up, named Matt Hannah. He said, “Aren’t you Jenna Lyons?” Later on, he asked for my number, saying he was wondering if I’d be interested in TV. When he called, I said, “Look, I don’t have a job. No one’s been calling. Take me to lunch.”
I told him that I don’t know anything about television and I don’t think I’d be good on TV. And I don’t want to do reality TV. But we realized that we had a good conversation around the fact that there wasn’t really anything that did fashion, home, beauty. And there wasn’t anything that felt honest. Everything felt constructed. There were a lot of makeover shows, but they all had a similar vibe. Along the way, I was very concerned with it not being cheesy. The show was originally going to be on TNT. But, after they saw the edit, they said, ‘We think this show would be better on HBO.’ They were thinking it would be a little bit more... sparkly. The way reality television is.
The show is a hybrid of reality TV and documentary, and a big part of it is you trying out prospective employees. How did the casting work?
One of the biggest challenges was that we wanted to make a hybrid of a reality show and a documentary, and we originally had two different [production] teams—we had people whose background was reality and people whose background was documentary. Everyone was on board. Everyone was excited. But it just didn’t work, because they both had different ways of going about it. The biggest conversations we had were around the casting. In reality TV, there are no stakes. You’re casting for just who’s going to make good TV. But, for this, we were casting for people whom we wanted to work with. It was a weird process. Many of the people came onto the show through word of mouth, but they all had to go through a traditional casting agent. The casting agents were trying to see how spicy they were, and how good they’d be on TV.
In one episode, you admit how difficult it was to leave J.Crew, but you also say that you wish you’d done it earlier. Can you talk more about that?
I think that I could have probably exited two to three years earlier, and it might have been better. The business was struggling at the time. There’s this thing that happens when you are in a company you are charged with, and feel responsible for the team. When that is the case, and things get bad, you don’t want to go. But then, of course, when things are really great, you don’t want to go, either. How do you find the right time? It is really hard. And I’d been there for so long that I feel like I’d got to the point where I was no longer as effective as I’d wanted to be.
I had so many people who were my senior team members. I’d been with them for fifteen, twenty years. At the office, we had one of those half walls that didn’t go up—I remember hearing some of my team saying, “Oh, we’re not going to show her that. She’ll never go for that.” And what I realized was that, in a time when we needed to make changes, I needed to think differently and be open. But the mere fact that I had team members who’d been with me for so long—they weren’t even going to propose things. They were going to assume I’d say no—and rightly so. I might be standing in the way of shift, because just my mere presence means that people might not think outside of the box they’ve been in, because they’re, like, “Oh, this is the box that works for Jenna.” That’s not good for the company. I really struggled with that.
You say that, after you left J.Crew, nobody was calling you. And you were pretty quiet from 2017 until this year. What were you doing during that time?
The first year, I was so depressed. I realized that everything I did, everything I knew, everything I was invited to—it wasn’t because of me. It was because of my job and my title. It was false for me to think that it was because of me. But you convince yourself along the way. And you have to be careful of that. I really sat there and realized, Oh, none of this is because of me. And so what am I now? What do I have?
I remember my son, Beckett, who is lying on the bed here next to me—I thought he’d be so excited to have me home. But I wasn’t home whipping up ten-course meals and playing games. I was kind of just sitting on the couch and having a hard time. I thought it would be nice to just be around, but he seemed far more interested in me when I started to work again and he saw people in the house and exciting things happening. The first year—and I say this with real honesty—I sat on my couch. I didn’t take pottery classes. I didn’t learn to speak French better. I didn’t make bread. In that moment, I felt kind of embarrassed that I wasn’t doing anything. But now, looking back, I needed to be quiet.
