Jenna Lyons on Her New TV Show, Stylish With Jenna Lyons

In 2013, during her “heyday” at J.Crew, Jenna Lyons was given an impressive title by The New York Times: “The Woman Who Dresses America.” Seven years later, she’s no longer selling us cashmere sweaters and rolled-up chinos as J.Crew’s president—she left in 2017—but no one’s exactly come for her title, either. In 2020, there isn’t a single person or brand shaping the look of American fashion, nor is it reasonable to expect someone to do it the way Lyons did. A perfect storm of Instagram, fast fashion competitors, and e-commerce was chipping away at J.Crew’s market share when she left, and things have only gotten more decentralized since then.

Lyons is the first to say that’s a good thing. “More people can play [the game] now, which I think is incredible,” she said on a recent call. “There’s something really magical happening, but it’s also very challenging. We have this phenomenon of the internet and Instagram, which are great, because if you’re someone who doesn’t live near the best stores in New York, you can still see everything online,” she explains. “However, you’re really seeing everything.” We’ve never had more designers, more clothes, or easier access to them; a Google search for “women’s cashmere sweater” pulls up 18,000,000 results. How could you not be overwhelmed? “There are so many options, and I think it makes it even more confusing for people to figure out, what do I do?” Lyons says.

If Lyons isn’t dressing us literally, she’s still styling us, let’s say subliminally. Her legacy at J.Crew wasn’t a particular product, it was the way she inspired women everywhere—from Michelle Obama to young girls in the Midwest, like this writer—to have fun with fashion, dress intuitively, and ignore the rules. She made print-mixing, daytime sequins, neon lipstick, and “high-low” dressing—like the denim jacket and taffeta ball skirt she wore to the Met Gala in 2012—the building blocks of 2010s style. Lyons and her team (“It’s really hard to get people to print this, but I get far more credit than I deserve!” she insists) made daywear feel special, and eveningwear feel cool. And while she admits they occasionally “took things too far,” the concept remains relevant. Women still don’t want to look overdone, and there’s a Lyons-ish irony in the way girls mix sneakers with dresses today, or hoodies over skirts.

Lyons said the most satisfying part of her former life was helping women find their style and confidence, the same way fashion helped her find her voice as a shy, awkward child who “never fit in.” “The reason I got into fashion was to help people,” she says. “We called ourselves ‘creative services’ at J.Crew, because we were there to support the customer and make things more beautiful. I really enjoy the power of transformation, and how internally you can feel different if you feel beautiful and like yourself. It can be so meaningful.”

Over the past three years, she’s been doing just that: helping friends feel like themselves in their clothes—and their homes. Some needed help putting an outfit together for a graduation or black-tie dinner, and others wanted her guidance on their renovations, another passion of Lyons’s (lest you forget the Pinterest frenzy sparked by her Park Slope brownstone). “These people all had different budgets—literally low, medium, and high—and they were all struggling with the exact same issues. They didn’t know what lighting to use, or how to choose the right marble, or what kind of paint finish to pick, or where to buy a rug…They might want a velvet couch, but is it a cotton, silk, or mohair velvet? Is it shiny or matte? They just hadn’t done any of it before,” she explains. “I thought that was interesting, and maybe there was something there.”

That “something” turned out to be her new business, Jenna Lyons L.A.D. (which stands for Life After Death). You might formally describe it as a design firm; less formally, as a one-stop shop for all things fashion, home, and beauty through the Lyons lens. The early days of the business are documented in a new HBO Max series, Stylish With Jenna Lyons, out December 3, a reality-slash-competition show that follows young women and men competing for a job with Lyons and her team of Sarah Clary and Kyle DeFord (both former J.Crew colleagues). They participate in challenges like decorating a Brooklyn brownstone, creating a monochrome look that’s up to Lyons’s standards, organizing a dinner party in Los Angeles, finding local makers to stock in a pop-up store, and assisting in makeovers.

This isn’t the cutthroat, tearful kind of competition show we’ve grown accustomed to. In most cases, the challenges function more like style lessons, with Lyons critiquing submissions and suggesting improvements. The furniture and decor two contestants sourced for the brownstone were too cold and modern for the space; a place card on a table setting hadn’t been properly glued, an oversight that would never get past Lyons, who’s known for her acute attention to detail. (Her “peony folder,” a document she made for a past assistant with photos of the ideal peony colors and sizes, will no doubt go viral when Stylish airs.)

The competition isn’t the main storyline: The show’s narrative winds between the contestants and Lyons’s own projects, like designing the photo booth at the 2020 SAG Awards and launching LoveSeen, her new line of false eyelashes with the makeup artist behind J.Crew’s signature poppy lip, Troi Ollivierre. She also gives styling and interiors advice throughout the show, with photos reminiscent of her J.Crew catalogues: how to mix textures, how to wear oversized proportions, and why you should wear your “special pieces” even on un-special days.

“I think there’s a lot of fear around what people ‘should’ wear, and this fear of asking questions,” Lyons says. “It never occurred to me that I’d be doing TV, but when we talked about making a reality show, my caveat was that it actually has to be real. I didn’t want to fake it or create drama that isn’t there, and I wanted to give people real challenges. If I’m going to hire someone, I want to see what they can actually do. That was an added level of intensity, but it also allowed people to see that not everyone feels confident. They don’t always know what to do, and that’s okay.”

One episode sees Lyons pitch an investor on a shoppable lifestyle website with editorials focused on event planning, outfit ideas, decorating tips, and more. When COVID-19 hit, it became less of a possibility—at least for the moment—since Lyons couldn’t build a team or produce shoots. But the idea is certainly viable; Lyons is the O.G. influencer. (Next week, ahead of the show’s premiere, she’s launching an online pop-up shop with home, beauty, and fashion items by local makers—perhaps a test of what the website could become.)

You’ll get plenty of ideas from the show, too, which was filming right up until the spring of this year. Fans of Lyons’s style might be curious to see how it’s evolved over the years; she describes it as “slightly quieter” now, and wears a lot of blazers and button-downs in the show, often accessorized with a silk ribbon in her hair. COVID-19 has had an impact on Lyons’s aesthetic of late, as it has for all of us; on our call, she said she’s been doing a lot of browsing at Westerlind, the outdoor apparel shop in Nolita. “I’m obsessed with socks, sneakers, men’s clothes, camping gear… I barely recognize myself!” she joked. (Suffice it to say, her five-inch heels are getting a break.) “I’m walking and taking the subway everywhere now, and I want to be able to just go.”

You can watch the Stylish With Jenna Lyons trailer exclusively here, and catch the full series on HBO Max on December 3rd.