Style

Jenna Lyons

Jenna Lyons on Life after J.Crew and Building Her Empire from the Ground Up

In partnership with our friends at HBO Max

Technically, Jenna Lyons was “influencing” before influencing was even a thing: The signature oversize frames, the hyperpolished hair, the eccentric yet somehow totally approachable style. And then, of course, those fire-engine-red lips that exude power, magnetism, and sophistication.

“It’s ironic because a lot of how my look happened was out of absolute necessity,” insists Lyons. “When I had a baby, my hair started getting thinner and my son started clawing at it when breastfeeding, so I started to put it up. And then separately, I fell up the stairs twice because I was looking at my phone—I misjudged the steps and scraped my shins—so I started wearing progressive lenses.”

Revered for her nearly three-decades-long reign as the queen of America’s OG sweetheart company, J.Crew (she dressed Michelle Obama, too), she’s totally unpretentious, even self-deprecating at times. Lyons is quick to credit so much of her sharp, discerning eye to her J.Crew mentors, who hired her straight out of Parsons School of Design at twenty-one.

“I learned so much about how to see and how to edit from the two people I worked for at the beginning of my career, Scott Formby and Emily Wood,” she says. “They gave me that foundation.”

Jenna Lyons in workshop Jenna in front of camera

And yet, it’s apparent with the launch of her latest creative venture, Sort of Creative, that the student has become the master. Fans from around the world will soon be able to observe as Lyons builds her new creative empire from the ground up. That’s because this time, she’s calling the shots on camera.

“It’s basically me, my team, and our associates that help me transform spaces and make people over,” says Lyons, describing her part-reality, part-competition television show, Stylish with Jenna Lyons, streaming now on HBO Max. “You get an intimate view of the creative process: how we’re doing it, how we’re not doing it. It’s very honest.”

The thing about Lyons is that whether she’s styling an outfit, pulling together a room, or launching a beauty brand (see: her new false-lash line LoveSeen), everything she touches turns to sparkly, sequin-y gold. When asked what it’s like to wear so many hats, her answer could not be more her: “You know what’s really weird? I actually look terrible in hats.”

Sure, she may reflect on her sudden departure from J.Crew with mixed feelings, but it’s clear that the magic of those heyday years wasn’t just the brand; it was her. As for the long, perfectly feathered, natural-looking lashes? You can add them to her should-be-trademarked look.

Scroll on for more of our conversation and stream Stylish with Jenna Lyons now on HBO Max.

REAL TALK WITH
JENNA LYONS

Q

Tell us about the show—we bet your friends are excited to see you on TV.

A

Oh, I don’t know about that! I think they’ll be running for the hills. But it’s focused on fashion, home, and beauty. I didn’t want the competition element to feel staged, so we thought, Well, what if we built a team and the competition becomes about hiring? So we added that element to it, but I wanted it to be real—I wanted my team to have real time and real money to work with. You see us making lots of mistakes and also doing some things right. It’s reality television, but it’s a different kind of reality television.

Q

You talk about the fear of failure being magnified in a public forum—how do you not let fear get in the way?

A

In this world where our Instagram lives present a life that’s not really real, it’s refreshing when people are transparent and honest and show you their faults. I find that when people just come out and say, “Here’s what I got, here’s where I struggled, and it’s not perfect,” that’s what I relate to. Success does not come without failure. There is not one person who tries new things and puts themselves out there who doesn’t fail. And that’s okay.

Q

Do you approach interiors differently than you do clothing?

A

There is so much emotion attached to clothing. When you’re dressing a person, it’s a different thing from picking out a couch. The couch isn’t going to look in the mirror and say, “Oh no, I look bad.” There is a lot of emotional weight that goes with dressing a person. The goal is to care for that person intently and make sure that they feel beautiful and seen and loved. Putting together a room doesn’t have that same attachment, but the process is almost identical.

So many of the basic building blocks of building an outfit and mixing it up are the same tenets that I try to follow when doing interiors. And I’m not an interior designer—let’s just call a spade a spade. But part of what I love about this new world is that you don’t have to be deemed as such. For me, it’s like, “Here’s what I do; here’s what I like.” And if you like it, that’s great. At the end of the day, I like to put things together, and I’m super open to trying new things.

Q

Why do we feel the need to put ourselves in a singular box?

A

Do not put baby in a box! I remember distinctly when I was young, filling out one of those questionnaires about what you want to be when you grow up. There was a box for teacher, doctor, lawyer…there wasn’t a single creative option on there, and I was so terrified that I had to fall into one of those categories. I remember writing “art director” under the “other” section—it’s so ironic, I didn’t even know what that meant at the time. I was ten!

Q

How do you find inspiration these days? Does social media play a part?

A

I use social media in a very specific way. I have a tendency to deep-dive into things. It’s funny because I watch my Instagram algorithm shift based on what I’m working on. I’m doing a hotel project in the Bahamas, and I’ve been looking at 80 million pictures of rattan-and-cane chairs. Now my entire feed is rattan-and-cane chairs. But I love that I can find people that I would never have seen before. We’re doing a pop-up for the final episode of the show and I was researching ceramics and found this amazing woman out of South Africa, and I never would have found her stuff otherwise. It’s kind of incredible.

Q

Do you feel like your style is evolving?

A

I think it’s softening up a bit. A couple of years ago, I went out to a restaurant with my hair down and I had on an old pair of glasses that were very delicate. Someone came up to me and said, “Oh, I didn’t recognize you!” And I thought, Amazing. I marched over to the glasses store and bought six pairs of completely different frames. But I’d say my mantra for getting dressed these days is: How many times have I worn it, and is it clean? I’ve been in a state of purging lately, but not in a Marie Kondo way because I love clothes and there are certain things I’ll hold on to because they really do bring me joy.

Q

As someone with such impeccable taste, do you find that taste is something that can be taught?

A

I think it can be honed for sure. There’s a woman on the show whom I work with, Sarah Clary, who could put on a paper bag and look phenomenal. And I’m just not that person. I’m more studied than that. I think about it, but I also really enjoy it. We’re told how to be, what to wear, and what to do all the time. And for me, it’s more important to teach people how to look for themselves: How does it feel? What does it do for you? Do you like the silhouette? Does it feel flattering?

Q

Is the goal with your company to teach people how to cultivate their own sense of style?

A

With design, there are certain places people get stuck. Something I talk a lot about on the show are sightlines. When you look down the hallway, what do you see? Do you like what you see? Look at it from every angle. Is it too cluttered? Is the light low? I try to give people starting points because it’s not helpful for me to just redo everything and make it pretty. The idea is to give tips, big or small, for ways you can train your eye to see things differently so that you can make your own decisions.

Q

Were you always interested in the beauty space? What turned you on to starting a lash line?

A

I’ve always been interested in eyelashes because honestly, I don’t have any. Before I left J.Crew, I noticed that many of the women wore little to no makeup, but they were all coming to work with lash extensions. And at the same time, all of these Instagrammers were doing these dramatic video tutorials where they would put on seventeen layers of contour and highlighter and eye shadow. Then at the very end, they would pop on their eyelashes. I thought that was so interesting. Here are two completely opposite ends of the spectrum, but they are both focused on eyelashes as the finishing touch. I can’t do the no-makeup thing because I’m not Gwyneth Paltrow, and I also can’t wear ten layers of contour because I’m old. So I thought, Is there something in between for someone like me? LoveSeen was born out of that.

Q

What’s been the best part about getting to flex your creative muscles in all of these different areas?

A

It’s really scary leaving the landscape of a job that you know so well without that safety net of: What am I going to do next? And: Where will I land? But I feel lucky and grateful that I have an opportunity to try new things and feel like I’m still learning. And I’m getting to do it in a way that leans on my past experience, which is incredible.

Q

Any advice for people who might feel creatively unfulfilled or afraid to try something new?

A

I’m terrible at taking and giving advice. But the one thing I will say is having curiosity around things outside of the one thing you’re currently doing is important. And being voraciously into anything that excites you is important. That is the thing that you should be doing in your spare time. That’s what’s going to keep you engaged. And that’s probably the thing that you’re going to kick ass at, too.

IN JENNA’S CART