From ‘dressing America’ to ‘crickets’ and back: Former J.Crew guru Jenna Lyons on failure, curiosity, and influencer culture

“Crickets.”

That’s how Jenna Lyons describes the anticlimactic time period following her departure from J.Crew, where the New York fashion executive spent the last 27 years of her professional life.

“I sat on my couch and I was like, maybe someone will call today [with an offer]. Maybe someone will call tomorrow. It was quiet. So quiet.”

However unexpected, Lyons found the silence empowering. It got the former creative director thinking about a podcast that laid out a social experiment where five people are placed in a room with bricks, books, and art supplies. “And then they put another group of people in [another room] with the same art supplies and bricks, but no inspirational reading material. They were only given a phone book. The team that had all of the inspirational material made things they’d already seen in life. But the team that had no inspiration, nothing to look at, had done really creative things. They had ground the bricks down and recreated little sculptures. They had to think for themselves.They kind of just got to craft.”

In her own proverbial room with no “inspirational material”, Lyons had the chance to really ask herself, “What does make me happy? What do I really want to do?”

She’s still figuring that out. But she’s a lot farther along into the process these days. She’s designing a hotel in the Bahamas; she founded Sort Of Creative (formerly known as Lyons L.A.D., or “Life After Death”) – a creative agency that tackles interior design, fashion, and beauty; she launched a lash line (LoveSeen); she’s even become a reality TV personality now, starring in HBO Max’s Stylish with Jenna Lyons, which chronicles her building the new agency’s creative team.

Although she spent nearly three decades in the fashion space at J.Crew, Lyons frequently points out how “interconnected” personal style, interior design, and beauty can be. “I think the way that you approach a home is very similar to how you approach an outfit is very similar to the way that you think about beauty,” Lyons says. “And they were very connected in my previous life, whether it be the design of the stores or doing my own homes. And also the way that we approached the beauty for J.Crew … You don't think about a fashion show without the set, the music, the makeup, the hair. It’s all part of the experience.”

That holistic point of view was reflected in every aspect of her earlier role with J.Crew, which hired her straight out of Parsons School of Design in the early 1990s. Lyons rose through the ranks, becoming vice president of Women's Design in 2003. By 2008, company chairman and CEO Millard Drexler appointed Lyons as executive creative director; in 2010, she became president of the company as well.

For nearly the entire 2010s, Lyons’ aesthetic vision determined the look and feel of J.Crew’s (not to mention Madewell and J.Crew Factory) Style Guide. Her fashionably gawky, bespectacled appearance – once the source of childhood shame and bullying – was now the look everyone wanted to emulate. Her influence expanded well beyond J.Crew: in 2013, The New York Times dubbed Lyons “the woman who dresses America”; Michelle Obama frequently wore J.Crew during her time in the White House; and Lyons even popped up in New York-based TV shows (she memorably played Lena Dunham’s boss in a few episodes of Girls). In short, Lyons’ name became synonymous with a type of effortless, affordable – but still edgy-cool – fashion.

In April 2017, however, Lyons and Drexler agreed “it was time for a change”. On her own for the first time in her career, Lyons admitted she’d never even considered going out on her own, even in the years leading up to her departure. “I was president of J.Crew Group, which meant I was overseeing all three brands. So there was J.Crew, Madewell, and [J.Crew] Factory. I barely had time to go to the bathroom, much less be strategic about my future.”

Once Lyons did start to take lunches and brainstorm her next move, it was actually Anna Wintour who suggested she do a reality show. “I think you should do TV, not fashion,” the Vogue chief told Lyons. “You’re good on TV.” Now, viewers can watch Lyons in action on Stylish, where she tackles seemingly everything, from hiring creative associates by seeing how they do with short-form design “challenges” to completely redecorating friends’ Manhattan townhomes.

When it comes to reimagining a space, which, when televised, typically takes place over a very short period of time, the details-obsessed Lyons is crystal clear that absolutely no corners are cut in the interest of hitting a deadline. She and her team, which also comprises chief of staff Kyle DeFord and stylist Sarah Clary, go hard on mapping out their strategy before starting on any project, teasing out every detail with a “fine-tooth comb”.

“The network was great about really making sure that we have real money to do these projects,” she says. Exposure via a premium streaming network also helps incentivise artists and decorators to give her a good deal, Lyons infers, mentioning how fine arts painter Dean Barger “did us a favour” in the series premiere by painting a delicate mural on the wall of her friend’s townhome. Lyons likewise points out that none of her projects required any construction. “That’s where you really run into challenges,” she says.

“I think that there are ways to reimagine the space that doesn't require ripping down walls. And how do you do that if you can't afford it? Or you just aren't up for that? It takes a lot of time and most people cannot renovate. How do you be creative in a scenario where you've got to work with what you've got?”

Though there are no shortage of good styling tips to absorb, watching Lyons conduct an interview is particularly entertaining. In one episode, she sits down with Instagram personality Alyssa Coscarelli to assess her for a role in the burgeoning company. When Coscarelli introduces herself as an “influencer”, Lyons visibly cringes (but does end up hiring Coscarelli for a table-setting photo shoot). When asked about her overall view on influencer culture, Lyons chooses her words carefully.

“I think the thing that feels a little bit tricky to me – and when I say tricky, I just mean it's harder for me to connect to – I do think that there's got to be something where, what is it that you do?” Lyons muses.

“For instance, I love watching makeup tutorials. Like makeup artists Erin Parsons or Mary Greenwell. In my mind, they're influencers because they are actually helping you, giving you something,” she continues.

“If you're going to give an opinion and give a critique, that's cool too. I'm all for that. But I think you need to know your stuff. I think where I lose connection to it is when there isn't depth of knowledge or depth of interest. And it's just, you know, posting pictures of yourself, like, okay, like fine. I just, I don't know how influential that actually is.”

Aside from getting a closer look at Lyons’ process – in the creative and business spheres –perhaps the most fascinating part of Stylish is the more intimate portrait of the woman herself, behind the massive eyeglass frames and bright lipstick. Though she is generally portrayed as a high-powered Girlboss-with-a-capital-G, Stylish is careful to emphasise Lyons’ relatability. As a gawky, rail-thin teen who suffered from a rare genetic disorder called incontinentia pigmenti, which can cause skin scarring, hair loss, and malformed teeth (Lyons has said that she wears dentures), Lyons spent the earliest part of her life feeling anything but beautiful. Fast-forward a few decades, and Lyons’ mismatched, geek-chic, edgy-tailored look still reigns supreme even three years after leaving her post at J.Crew.

If Lyons’ career hallmark is reinventing closet classics for a new generation, she doesn’t necessarily expect that her Sort Of Creative team members share her exact aesthetic. All she asks is that anyone who comes to work for her has a defined perspective of their own. What would they do in a room that contains only bricks and a phone book?

"You can help mold or sculpt someone's style. What you can't do is make someone curious,” she says. “You can't make them passionate or really enthusiastic. Being open to things that aren't necessarily [how] you've already seen before. That requires a certain amount of openness.

“Creativity does not exist without failure,” she continues. “If everyone knew exactly what they were doing and had everything lined up, then there would be no sense of discovery and there'd be no change. There’d be no progress.”