Step into the universe of the coolest creatives in the fashion industry with our series My World, where readers will discover how the top stylists, designers, and tastemakers built their careers; their favorite under-the-radar restaurants and hotels, beloved deep-cut album, and fashion finds; etiquette rules they stand by; and so much more.
No one has shone their light on modern American fashion quite like Jenna Lyons. Crowned by The New York Times as “the woman who dresses America” during her 27-year tenure as creative director and president of J.Crew, she revolutionized how American women dressed with her avant-garde approach to style and encouraged a whole generation to embrace wearing sequins with stripes, feathers with classic button-downs, hot-pink satin with denim, and distressed jeans with tuxedo jackets. Lyons unquestionably gave J.Crew both mass appeal and a cult fashion following with her preppy-glam, geek-chic aesthetic. Since closing the chapter at J.Crew, the fashion icon has turned her sharp mind to a whole host of other projects—including her own false-eyelash brand, LoveSeen—and has captivated audiences with her humor and honesty on reality television and social media. More recently, she has joined forces with luxury eyewear brand Dita to design the aptly named Lyons frame for those who seek to make a statement with their eyewear. It is inspired by her signature look—which, much like Lyons herself, is both timeless and contemporary.
Lyons’s career highlights are of the type a fashion person could only dream of. She was widely recognized as the creative force and the main driver behind J.Crew’s phenomenal rise from floundering retail business to one of the most coveted brands in the U.S. During that time, she was championed by the likes of Anna Wintour and had the honor of dressing Michelle Obama and the First Family in head-to-toe J.Crew for the 2009 inauguration. But it was perhaps her very own legendary style moments and iconic looks (think the famously styled feather skirt, white shirt, and mink coat she wore to Solange Knowles’s wedding) that secured her spot as an American fashion icon, and she continues to be pinned on the style mood boards of fashion devotees across generations.
Today, it’s Lyons’s vulnerability, honesty, and unfiltered personality that we get to see on-screen, on Instagram, and in interviews that make us love her even more. She has openly discussed the difficult transition after leaving J.Crew and her journey of reinventing herself later in her career. She continues to captivate audiences with her bold yet refined aesthetic that blends high fashion with everyday wear. Her passion for her consulting projects with brands, her creative endeavors on- and off-screen, and her recent eyewear collaboration with Dita is unmistakable. We sat down to discuss her work, wardrobe, signature beauty look, and everything in between. Ahead, you’ll get a glimpse into Jenna Lyons’s world, including her wardrobe staples, her favorite NYC spots, the exact color of her signature poppy-red lipstick, and so much more.
(Image credit: @ditaeyewear; Getty Images; @jennalyonsnyc)
Give us a peek into your own world. What does the day-to-day in the life of a creative entrepreneur, television personality, and all-round fashion icon entail?
Even in my previous job [and] even though I was working at one place, I was managing three different companies—J.Crew, Madewell, and J.Crew Factory—so every meeting was different. I found myself going from a meeting about the models and fittings for Madewell, then we would go to a budget meeting for J.Crew, and then we were going to a marketing meeting for Factory, and then I’d be going into a strategy meeting planning for the next couple of years. There was always so much variation, and truthfully, I think I realized I’m more comfortable in that because I find myself inserting myself into many different things so I can actually have my hands in a lot of different projects. Nowadays, it’s pretty varied. I wouldn’t say any day looks the same. I do consulting work, so it can be a strategy meeting for other companies. Then sometimes, it’s interviewing people. Sometimes, it’s being interviewed. Sometimes, I’m shooting things about outfits. Some of it is going on TV. It’s really varied, which I really enjoy.
Your time as creative director at J.Crew put you on the fashion map—what were some of the highlights of working at J.Crew, and how did it shape your career and who you are today?
It was some of the most incredible moments! Having the opportunity to dress the First Family of the United States was really just an insane honor—not just because it was the First Family but because it was the Obamas. Just the way that they integrated fashion and that kind of connectivity to people into their lives, it was really unusual. I mean, if you look at any of the First Ladies or First Families prior, you never knew where they got their clothes, or if you did, it was high-end couture, and it wasn’t accessible to the general public. This is really the first time you saw a First Lady, in particular, going on a national television show and saying, “Oh, I bought this at J.Crew.” By establishing that connection with people in the country, it also established a connection with us, and it just opened up a whole new experience for myself and for the team to feel so much more connected to people. People that didn’t necessarily think that the product was for them, all of a sudden, were more open to asking about something they could wear. This was really a very exciting moment.
I think being a sponsor for the CFDA/Vogue Fashion Fund was also incredibly exciting for everyone—not just me but for everyone on the team. We got to work with designers like Joseph Altuzarra and Jennifer Fisher and The Elder Statesman, and it gave the team and myself this whole other opportunity to give back and share but also then to highlight designers who were up-and-coming, and that was just a really incredible experience. To have the opportunity to work with people who just think really differently, that was just so fun.
You are now a much adored television personality—we love watching your humor and style shine on-screen. Was moving into television an organic next step in your career? How do you pick and choose your on-screen projects?
I think it was organic in the sense that there were not a lot of choices. When I left J.Crew, I really thought I was going to get another fashion job. While I was scared of getting another fashion job, I just assumed that that’s what I would do. And then I realized that it wasn’t really as easy as you might think, and a lot of the brands here in the United States just associated me with J.Crew and didn’t really see a way for me to integrate into their brands. I found myself thinking, “Gosh, I don’t think I’m going to do fashion again,” which, in some ways, was a relief and then also kind of scary. So I just started taking meetings—anyone who wanted to meet with me. I was like, “Sure, let’s talk,” and I opened myself up to whatever came my way and didn’t filter. That led to some really unusual and interesting conversations. One of those conversations ended up in California, sitting in a restaurant, and someone walked up to me and said, “Hey, can I talk to you about a TV show?” I was like, “I don’t know anything about TV!” But I just went with it on a whim. It was not the most strategic thing, but it was an incredible experience, and I’m so happy I did it. In terms of how I choose now, mostly, I think, “What is the most provocative, unexpected thing I can do?” That will probably be the answer!
You recently collaborated with luxury eyewear brand Dita to create a new limited-edition frame embodying your signature style. How did this exciting collaboration come about, and what was the inspiration, creative process, and design philosophy behind this exclusive release?
It’s so funny—it was not even a collaboration but more like an insistence on my behalf! I had purchased their frames years ago. They were sunglasses, and I had made them into eyeglasses, and then I bought every one they had. They had some sort of problem with them in manufacturing, so they discontinued them. I continued to wear them, and they would repair them for me. … When I would lose them or break them, I said, “Please, make them for me again,” and they said they couldn’t. I finally insisted, and that’s how the collaboration came about in the end. It wasn’t like them coming to me and saying, “Oh, we want to work with you.” I just needed to figure it out and make it happen!
I tried so many other brands, and I couldn’t find anything that was classic but also larger because their sunglasses are a little bigger in size. When we finally decided to relaunch it, we rebuilt the frame at an incredible Japanese factory where the quality of what they do is very special. Then we worked on color options. I really love color, and I was able to go to their offices in California and work with their team, and that was so fun. I wear the soft-pink/amber color, and we also have a charcoal style, which gives some depth when you’re wearing it. The lens is a graded mirror, so you can still see through it quite well, but you get a little bit of a sunglass vibe without having that dark shade.
What would be your next dream project or career move—whether in television, fashion, or anything else?
I’ve been watching the musical chairs of all of the designers happening around, and I do think that there’s a lot of houses that are here in the United States that are coming up that are so interesting to me. If you’d asked me five years ago, I would have said I would love to work at Ralph Lauren, but I think that ship has sailed. I don’t think it’s the right thing now, but I’ve often thought about that. I think it’s such an incredible brand, and Ralph has done such an amazing job at creating a visual language that has been really unchallenged. He really sets the tone for what American fashion has become and has stayed for a very long time. But I don’t know if that would make sense now for me.
Now, I’m much more interested in doing than I am in directing. I had the opportunity to direct, but when you get to a point where you’re managing such a big team, you’re not doing as much anymore. I think what I love about some of the consulting work that I’ve been doing is I get to be much closer to the process and the actual doing in the product and really having conversations about what something could be, should be, and what the strategy around that could be. I love that part of the process. I still like TV, so I wouldn’t mind doing more TV, but we’ll see what happens.
j.crew
Faux-Fur Lady Jacket
john hardy
Spear Flex Cuff
(Image credit: Getty Images; @marialarosa_official; Coliena Rentmeester/Trunk Archive)
You are a true fashion icon and were once referred to as the “woman who dresses America.” Do you have a go-to fashion uniform?
I never loved the idea of a uniform. My favorite thing was dressing up and wearing something different every day. … After leaving J.Crew and after COVID, I find I wear suits pretty consistently. I have a whole slew of men’s suits, and I honestly feel the most comfortable in them. That’s become my go-to.
What are the wardrobe staples you live in every day? Why?
I have all my shirts custom-made because I love custom-made shirts, and I find the process is so fun and love getting it monogrammed, etc. … Even on the weekends, I wear button-down shirts pretty much consistently. I get my custom shirts from Hong Kong. I started going there when I was probably 22. I remember the very first trip to Hong Kong I ever went on. I stayed at the Regent Hotel, and in the basement was a very high-end mall, and they have this custom-made shirtmaker, so I made my first custom shirt when I was 22, and I was like, “This is the best thing.”
I have to ask—do you have any favorite J.Crew pieces that you still wear and love today?
Oh, yeah. I mean, it’s nice to have some distance because when you’re in it, obviously, there’s the intensity and the intimacy of it all. When I first left, I didn’t wear a lot of my J.Crew clothes at the beginning, and now that I’ve had some distance, there are still pieces that I have, like these beautiful Super 120 flannel blazers I still pull off the rack. We did some really incredible embroidery, which I love. Also, when I worked on things for the Met ball, I have all those pieces and still wear them sometimes, and they were all made by the internal team. Yeah, [there are] a lot of pieces that I really hold dear and are special and will probably never get rid of.
You’ve worn so many iconic looks over the years. Is there a look that you look back on fondly? What’s the story behind how it came to life?
The one that I have the most love for myself and probably the one that I’ve gotten the most love for is the feather skirt that I wore with a white button-down shirt, and I wore it with a little mink coat over the top. That was a pretty quick throw-on outfit, and it ended up being one of the looks I have gotten more attention for than any other.
The skirt was from J.Crew. It was from our wedding collection. It was originally a wedding dress, and I wore it to the Met ball with a V-neck sweater. What had happened was I was invited to the ball, and I had never been before. I had no idea what I was doing. I was so overwhelmed at work, and I couldn’t think about it. I also was so intimidated because everyone was wearing full-length embroidered gowns, and people were spending years and hours and days and millions of dollars on these dresses, and I didn’t have access to that.
This wedding dress was hanging in my office. There was a conversation about what we were going to do with it, and the sample had come in quite expensive, and we didn’t think we were going to be able to reproduce it. I was like, “Let me just throw this on.” I threw it on, and it was a strapless dress. I was like, “I don’t think I can wear this,” but I just let it drop. I let it drop down, and then it was kind of a skirt, and I just happened to be wearing a V-neck sweater, and I loved the way the two pieces looked together. It happened by accident. I’ll never forget [this]: I get to the top of the stairs at the Met ball, and Anna Wintour was there with Stella McCartney, and Stella says in front of Anna, “Oh my God, you’re wearing a jumper. How lovely!” I was like, “Oh God, is this a good thing or a bad thing?” I was mortified. But apparently, it was provocative because I heard about it from the Vogue team later.
Which style icons are on your mood board? What do you love about them?
Paul Newman, Dua Lipa, Cate Blanchett, Charlotte Rampling—a whole splattering. With the women, they artfully mixed masculine and feminine, like they weren’t necessarily overly girly. There’s always this element of tailoring or something to anchor in some masculine dress that I really appreciate. I do think men’s clothes in and of themselves are just incredibly attractive, particularly on women.
Paul Newman, in the reverse, he didn’t dress as much like a man. He was softer and looser in his approach. He often wore fabrics that were softer, and things were a little bit unconstructed, which was not exactly what everyone else was doing. He skewed a little bit more toward a softness, and he really paid attention to tailoring and texture, which I think you don’t always see with men’s clothing. When you think of the dichotomy between those two groups, both are pushing toward the middle in some way yet not necessarily falling into strict identities of one or the other.
What’s the one luxury item you feel is worth the investment?
I think there’s no excuse for a bad jacket. Buy one beautiful blazer.
What’s your cheap-thrill fashion find that you love?
I love a pair of novelty socks like the ones from Maria La Rosa.
ralph lauren
Relaxed Cotton Shirt
You have a very distinct beauty look—red lip, slicked-back hair, and glasses. How did this Jenna Lyons look come about?
It was totally by accident and certainly was not strategic. It happened right after I had my son when I was breastfeeding. Every time I had my hair down, he would hold on to it and grip it in his fingers and pull it, and I thought, “I can’t have my hair down anymore.” It was too much. When I put my hair up in a ponytail, it looked kind of crunchy and rough. I would get up the next morning and not have time to do it, so I said “Okay, I’m just going to slick it back because it looks cleaner,” and then it just became easier. I realized that people were actually complimenting me and saying, “Oh, I love your hair slicked back.” Around the same time, I started getting photographed more frequently, and I noticed that I looked kind of dead in pictures—my skin didn’t have any color. I was tired and working a lot and not feeling my best. … One time, I popped on a red lip because I thought, “This will make me look a little brighter.” The picture turned out great, and I felt like total dog shit. I was exhausted. I had no color in my face, and I put on some blush and lipstick, and I looked so much better.
The glasses [were] just an accident too. I kept falling up the stairs because we had three floors at the office, and I was looking at my BlackBerry and taking my glasses on and off, and I always misjudged the steps. I was constantly losing them in the back of a cab or somewhere else, and finally, I realized I don’t have to keep taking them off. Once I did that, I just started wearing them all the time, so my look came about from the combination of those three things. It was not strategic. I wish I could say it was.
Everyone wants to know—what is your go-to red lipstick?
I have three that are my staples. One is a Sephora lip tar in Chili Pepper—basically, it does not come off. You put that stuff on your lips, and the good news is you can kiss anyone because it’s not going anywhere, and the bad news is it’s on. It’s not coming off. Then Nars Heat Wave is another one of my absolute favorites. And then there’s a Maybelline one that is glossy, which I don’t know the name of, but it’s the same kind of thing. It does not come off, but instead of being matte, [it] is a gloss, which I’m kind of into. I hadn’t wore a gloss in years, but my makeup artist introduced me to it, and I had never tried it. There’s another one from Korea. I went to Korea recently, and I have to say the makeup in Korea is amazing.
What’s on your vanity? What are your go-to skincare and beauty products?
I have a Shiseido face cream that I am obsessed with. It’s called Future Solution. This stuff is fantastic. I love it. My skin is dry and a little older, so I started using this stuff, and I’m totally obsessed. The Shiseido eye cream is the other one that is great. U Beauty makes this great tinted moisturizer that I’m obsessed with.
Any beauty tips and tricks you can share?
My secret weapon is wearing alcohol swabs underneath my armpits because it makes it not smell! I saw a doctor on TikTok, and she said the only reason we smell is because there’s bacteria underneath your arms, and this actually gets rid of it. It really works, and it stays! It’s so great. I don’t like getting deodorant on clothes, especially if I have to borrow something to wear or have something that I don’t want deodorant to get on—like anything satin or really fine fabrics. It’s so nice because it really protects the clothing from the odor and getting stained.
shiseido
Future Solution Cream
Nars
Lipstick in Heat Wave
Care Touch
Alcohol Prep Pads
What is the most prized possession in your home? Why?
I have a Cy Twombly drawing that I got when J.Crew launched in Paris. I was very fortunate to work with Yvon Lambert, who was a gallerist in Paris for years, and he asked every artist who ever did a show in Paris to do an authentic original poster for the show. One of them he had was Cy Twombly’s poster for his show in 1979, and he had the original drawing, and I was allowed to borrow pieces for our presentation to the French press. I sat underneath it for like a week of doing press, and I never wanted something so much in my entire life. I remember calling my financial advisor and saying, “I promise I won’t buy anything else ever!”
Finish the following sentence: My home wouldn’t be complete without __________.
All my animals: Popeye, Megatron, Rumba, and Charlie—my two kittens, my cat, and my dog.
Where is your favorite local spot that you’re most comfortable hanging out at?
My favorite place is the ice cream place—Van Leeuwen. I’m obsessed with ice cream. That and Sadelle’s—I spend an enormous amount of time at Sadelle’s.
You tend to travel a lot for work. What is the one hotel that feels like a home away from home? What makes it so comfortable?
It’s funny. I don’t go to the same places for work that frequently. One of my favorite hotels in Paris that I love is the Château Voltaire. It’s such a great small boutique hotel. It’s incredibly chic and very well situated. The last time I was there, Hailey Bieber was having her party on the ground floor, which is also really fun. I also do really love a Nobu hotel.
Lingua Franca
Puppy Love Sweater
creative candles
24-Inch Taper Candles
What are you watching right now?
I’m obsessed with Call My Agent! I wish there was another season. I just think French comedy is so brilliant. I also like Shrinking—that’s a cute show. And SNL is always a staple.
Is there a podcast or musician you are listening to that you love?
I love the podcast I’m Not Dead. It’s kind of new, but some of the people they’ve had on have been really interesting. Every interview they’ve done has been so well executed. They have really interesting people that are a little more unexpected.
Is there a specific book you’re reading at the moment? Would you recommend it?
I’m reading Sarah Hoover’s book called The Motherload: Episodes from the Brink of Motherhood. She is so raw—it’s great. For anyone that has a kid, it’s worth reading. She really lays it on the line.
What’s one thing on your queue that you haven’t gotten to yet but is next up for you (e.g., a specific show or book)?
Oh, that is a long list. I can’t keep up with The New Yorker—they’re stacked up on my nightstand. In terms of movies, I’m deeply excited for The Room Next Door with Tilda Swinton and Julianne Moore. I cannot wait.
Sarah Hoover
The Motherload
The New Yorker
Subscription
What is the one etiquette rule that you stand by?
No phones ever at the table. The phones are off the table, under the table. Not in your hands. Not for a kid. Not for an adult. Never.
What is your biggest pet peeve?
If I’m in a conversation with you, don’t check your phone. Just be here with me. Everyone understands if you don’t text back. You can just take the time and just be present.
What is something that’s overrated and underrated in your mind?
Underrated is oversharing. I think everyone should overshare. Cass and I joke about this all the time because we’re both oversharers, and oftentimes, oversharing is when you actually have fun conversations and can disarm a room and make someone feel comfortable. Please, overshare all day long. Overrated is being invited. Everyone wants to be invited to everything, and it’s kind of overrated!
If it were up to you, which fashion trend would never see the light of day again?
Manpris—men wearing capri pants! I can’t. That never needs to happen. And I’ve never really been a fan of a shrug.
What are your favorite things to give and get as gifts?
To give—little luxury items that you wouldn’t necessarily spend money on. I love giving beautiful socks like cashmere socks. I think those are things that no one wants to spend that kind of money [on], but it’s so nice to own them and have them and take them out on cold night—it’s such a luxury. I love giving something that I’d want to receive myself. I love giving candles. My favorite candles are these 30-inch candles, and they’re just so dramatic and beautiful, and they feel much more special than getting a 12-inch candle, which burns in a minute. Whereas these 30 inches, they come in like 30 and 24, and they’re just super elegant and beautiful. They’re from Creative Candles, and I love them.
