From her trend-setting career with J.Crew to the medley of new projects she has launched over the past year, Jenna Lyons has perpetually made the world a more stylish, joyful place.

Design Matters: Jenna Lyons

ENTREPRENEUR / CREATIVE DIRECTOR

2021

Jenna Lyons / Lyons Life After Death / Stylish With Jenna Lyons / LoveSeen / J.Crew / fashion / Parsons

Transcript


Debbie Millman:

Jenna Lyons started with J.Crew when she was 21 years old and worked her way up the ranks to become not only executive creative director, but also president of the company. Her style became J.Crew’s style, and her brand was synonymous with J.Crew’s. She was even appointed “The Woman Who Dresses America” by The New York Times.


Debbie Millman:

So, when J.Crew and Jenna Lyons parted company in 2017, they each had to figure out who they were on their own. Since the parting, Jenna Lyons has started a new eyelash company, and she is currently producing and starring in a new reality show on HBO Max. She joins me today to talk about her past, her present and her future. Jenna Lyons, welcome to Design Matters.


Jenna Lyons:

Hi, thank you so much for having me. I’m so excited to be here.


Debbie Millman:

Thank you, Jenna. Well, the first question I have for you is about your dog. Why did you name him Popeye?


Jenna Lyons:

That’s a great question. When I got Popeye, my son and I picked him out from a rescue place, and he was only two pounds. We wanted to give him a name that he could grow into and wanted him to be strong, so that was why we named him Popeye. And I understand that—


Debbie Millman:

You’re considering getting him his own agent?


Jenna Lyons:

It was a joke. But considering how much attention he gets, he may need one. He’s very, very popular.


Debbie Millman:

Yeah, he has a lot of charisma on the show, I have to say.


Jenna Lyons:

It’s so true. Ironically, he’s definitely my dog but when people come over, as soon as someone comes over and they sit on the couch, he looks at me and goes over and sits right next to them. Like, “Just so you know, mom, I can be friends with other people too.” It’s like he’s a total slut. I mean, I don’t know why but he totally give me a run for my money.


Debbie Millman:

Oh, I could tell you. We got a new dog a few months ago and he was also two pounds when we got him. He’s really a love muffin but only with us. He takes a while to get used to other people. Your dog goes and sits next to people, my dog barks at people. He’s now only seven pounds but you’d think he was a pitbull, the way he just is barky when he sees people he doesn’t like.


Jenna Lyons:

Well, the one thing I will say is your dog must be a puppy then.


Debbie Millman:

Yes.


Jenna Lyons:

OK, so Popeye did the same thing up until he was like 14 months. So, I think that goes away.


Debbie Millman:

Oh, good, because I want him to be a little bit more friendly—


Jenna Lyons:

I know.


Debbie Millman:

Although we do feel much safer now.


Jenna Lyons:

I don’t know if safe is really the feeling I get.


Debbie Millman:

So, Jenna, you were born Judith Lyons in Boston, MA, but your family moved to Palos Verdes when you were 4. When did you go from Judith to Jenna?


Jenna Lyons:

Oh, you did your homework. Well, I remember I went to Parsons. My first year in Parsons was actually in California, so it was Otis Parsons in Los Angeles the first year. I remember, I never really felt like a Judith. Well, the teacher said, “If anyone goes by a nickname or wants to change their name, now is the time to tell me. Roll call and I’ll put you in properly.” The girl in front of me, they get to her, and her name was Christina. She’s like, “Oh, I go by Sebastian.” I’m like, “Oh, shit.” All bets are off, I can do anything. I literally on that spot thought about what am I going to say. I had no idea. I didn’t know what to say. But my brother had teased me for quite some years, and he used to say, “Geni, geni, genitalia. Geni, geni, genitalia” as a joke. I know. Isn’t that a nice …


Debbie Millman:

That’s so awesome.


Jenna Lyons:

I mean, the derivation of my name is really sexy. It was the only thing that came to my mind, so I just said, “Jenna.”


Debbie Millman:

Oh, my god.


Jenna Lyons:

It just came out. And I wanted something, at least I had the same initial so I could sign my name. I got crazy.


Debbie Millman:

What does your brother think of this, that you took on his nickname, his moniker?


Jenna Lyons:

I do know that I didn’t tell a soul. I kept that a secret for, I don’t know, probably 20 years. I never told him until probably about five years ago because it was embarrassing. I don’t know, I didn’t really want anybody to know, so I’ve been keeping it a secret, but now I’m sharing it with you.


Debbie Millman:

Well, thank you. Thank you. Moving on to a slightly more somber note, your mother was a piano teacher and your parents got divorced when you were in junior high school. You’ve talked about a defining moment at that time in the tuna fish aisle in a supermarket.


Jenna Lyons:

Oh, gosh, you really went there. Yeah, I did. It’s interesting because my mom doesn’t remember this. You know how we all have those things in our head that completely strike us and someone else is there and they don’t have the same recollection, or it didn’t impact them at all?


Debbie Millman:

Yes.


Jenna Lyons:

I just remember being in the tuna fish aisle and me saying, “Oh, let’s get some tuna fish this week,” and my mom saying, “It’s a little expensive. Let’s not get it this week.”


Jenna Lyons:

Palos Verdes is known for being a rather fancy neighborhood, but I lived in the not fancy part of the neighborhood. With my father leaving and my mom doing the best she could on a piano teacher salary, things were always not easy. It was a very humiliating and humbling experience. I think, as a kid, I didn’t know how to process that. It was scary. It was a scary experience I had never had before. It really rocked me in a way. I don’t know how to express it.


Debbie Millman:

I know that that moment inspired you to feel that you could only rely on yourself. How did this manifest in your work ethic as you were growing up?


Jenna Lyons:

I think it was that coupled with a few other poignant moments, where my mother had said to me, “Make your own money. Don’t rely on anyone else.” I had made a really bad decision at one point where I had gotten money from a car accident and I bought my then-boyfriend a synthesizer. My mother lost her mind and was like, “Don’t spend your money on other people. Take care of yourself. You’ll never know. Don’t rely on other people and don’t overspend.” There were moments like that across my life that resonate with me.


Jenna Lyons:

I think it’s just, I know this is going to sound weird, but it was kind of just fear. It made me afraid that I would not be taken care of, and so I needed to do that myself. I also think I had a fear of just not doing a good job. It wasn’t just because I want to do well to make money. That was part of it, of course, to take care, but I also really had a lot of pride. I didn’t want to do a bad job. I didn’t want someone to look at something I did and say, “Ooh, that’s not good enough.” That was just something I didn’t feel comfortable with.


Debbie Millman:

Has it gotten any easier?


Jenna Lyons:

Oh, god. I mean, therapy helps, but …


Debbie Millman:

I’m still waiting for it to get easier. I’m waiting to feel safe. I just don’t know when it’s going to happen.


Jenna Lyons:

I don’t know if you ever fully sink into that, but it certainly is helpful to be a little bit more aware of it, particularly when you’re raising a kid.


Debbie Millman:

Yes. You were born with a genetic disorder called, I’m hoping I pronounce this correctly, incontinentia pigmenti?


Jenna Lyons:

Pigmenti, yeah. Very good.


Debbie Millman:

It impacted the growth of your teeth and your hair. You’ve said that as you were growing up you were ashamed of your condition. You also experienced tremendous bullying with your classmates, and I read that boys chased you and hit you in the schoolyard.


Jenna Lyons:

Yeah.


Debbie Millman:

Did anyone try and help you?


Jenna Lyons:

Listen, it was a different time. Just to be clear, it affects the skin and the teeth and the hair for people who don’t know it. My teeth grew in conical, that means like cones, so I literally looked like Dracula. I had huge bald spots in the back of my head that I didn’t actually realize were there until I was probably in fifth grade, and then my skin is kind of multicolored. It has darker patches and white patches, so I’ve got some sort of like vitiligo a little bit.


Debbie Millman:

Yeah, I have vitiligo, so yeah, I know what it is.


Jenna Lyons:

Oh, OK. So, there. This was years ago. This was long before people really talked about bullying. A lot of people talked about, “Don’t listen to them. You’re beautiful.”


Jenna Lyons:

It’s interesting, I’ve been doing a lot of reading. There’s this guy, Brad Reedy, who I’ve been reading some of his … I listened to some of his podcasts talking just about things you shouldn’t say to your kids, and one of them is “don’t listen to those people, you’re beautiful,” all those things because basically what it does is it shuts down this idea that you have pain. It’s basically just completely not acknowledging what you’re going through, and no one knew. My mother didn’t have access to that kind of therapy or perspective and people didn’t talk about bullying. I was afraid to go to my teachers. My mother didn’t know what to do. I didn’t want her to go to the school and then the kid that hit me get in trouble, and then he’d hate me even more.


Debbie Millman:

Yeah, made it worse. I know that. That happened to me too, which is not worth it.


Jenna Lyons:

There’s no way out of it, so I just kind of dealt, probably not in the best of ways.


Debbie Millman:

By the time you were in the seventh grade, you were six feet tall—


Jenna Lyons:

Yes.


Debbie Millman:

… and fashion was a challenge for you. You mostly had to shop in the big and tall section of stores. All that changed when you took a home economics class and you became fascinated by the world of sewing and making clothes. I read about a yellow round skirt printed with jumbo watermelons that you made. I was wondering if you could tell us more about that.


Jenna Lyons:

Gosh, you really … I’m so impressed. Yeah, I was incredibly tall and incredibly thin. I know that sounds like a blessing, but at the time, this was before there were skinny jeans for girls. There was no tall section for girls. I couldn’t wear pants and I had all these scars on my legs, so I was trying to hide them. I needed pants. I found myself just really unsure and buying really big clothes so that they would hang longer and fit. I thought I was a size 14, it turns out I was not.


Jenna Lyons:

And so, when I made that home economics class the thing, I wanted to make a skirt that would actually go to the ground because nothing would do that on me, and so I did the process of making something my own. I had to measure myself and then make the skirt to my measurements. I put it on, and I was like, “Oh, I’m not big. I’m actually kind of thin. This looks kind of good.” And then I wore it to school. The most popular girl in school, this girl Dara Peterson, sent me a note in social studies and was like, “Hey, I love your skirt. Where’d you get it?” I will never forget the moment.


Jenna Lyons:

I said, “Oh, I made it,” and she was like, “Would you make me one?” That was the first moment in my life where I had gotten positive feedback for the way I looked. On top of that, I made it myself. It was just kind of a little bit of like the best Pandora’s Box you could possibly open at that time in my life. I was really struggling. None of the boys wanted to go out with me because I was a head taller than all of them. Also, my teeth were still really not great, and I think, I’m sure, people looking at me were like, “I don’t want to kiss her.” It was just an incredible experience and I really, I ran with that one.


Debbie Millman:

I won the home economics award in high school, and the only reason I won, because we did cooking and sewing in home ec and I didn’t and still can’t cook, but my mother was a seamstress and my mom made clothes. She put an ad in the Penny Saver, and she made clothes for women that were tall and thin or people that couldn’t buy clothes anywhere else, and she would make their clothes.


Jenna Lyons:

Amazing.


Debbie Millman:

She would make all these beautiful drawings after she made them, and she hung them up in this little studio that was in our basement.


Jenna Lyons:

Oh, my god.


Debbie Millman:

We didn’t have any money, but she taught me how to sew and I would make all my own clothes, which I thought were the coolest. But, thinking back on it, they weren’t. It wasn’t like a beautiful, like the description that I read about the skirt, that it was long, liquid and cut on the bias with an elastic waistband and hand-stitched hem; the skirt turned out to be an epochal piece of rayon and mine were like pink polyester puffy sleeves with an applique purple butterfly.


Jenna Lyons:

Hey, that sound great.


Debbie Millman:

And I had a pair of red corduroy overalls.


Jenna Lyons:

I mean, yes. I mean, listen, I’m all in it. It sounds amazing, literally. I think there’s one year where I dressed in nothing but shades of purple, so have at it. I’m all for it.


Debbie Millman:

I still have that sewing skill but nothing like you.


Jenna Lyons:

Oh, no. I went to college for four years and one of the things we did was sew. It’s supposed to be like going to trade school, but I don’t know if I could sew that well anymore. I mean, it’s been a long time.


Debbie Millman:

Now, you’ve said you use clothing as an armor and that your personal style changes based on how you want to feel, even if you’re faking it. I know a lot of women do that. Like, I put on makeup today so that I would feel more confident talking to you face to face through Zoom. What makes you feel strongest?


Jenna Lyons:

It really depends on the moment and what the occasion is. I think I can give you an example. I am on the board of Shake Shack. They had a retreat and they asked if I would talk at the retreat. I realized that they all expected me to be businesslike and very professional, and so I chose to wear a sequined jacket that was incredibly sparkly in like 80 million different colors of sequins—it’s one of my favorite pieces—mostly just because I wanted people to see me feeling fun and relate. I didn’t want to be what they expected. I wanted them to see a fun part of me and a sparkly part of me, and that was important.


Jenna Lyons:

It really just depends on the moment. It doesn’t always work either. Sometimes I try really hard and I don’t feel great. It’s a process and an armor as such. I think … at the end of the day, confidence is an inside job. It can help. It can give you strength, but it doesn’t always give you everything.


Debbie Millman:

Your grandmother gave you a sewing machine and a subscription to Vogue. I read that the first copy you received was the 1982 issue with Isabella Rossellini on the cover and an Issey Miyake spread inside. You read the issues cover-to-cover, went back and read them again and even memorized the mastheads. Did you ever consider a career in publishing at that time working at a magazine?


Jenna Lyons:

I did not know anything about the fashion industry. I didn’t think that I would ever meet an Anna Wintour. I could not express to you how far away it felt from my life. I lived in an area like Palos Verdes when I was growing up. There were no bookstores, there were no magazine stores. The only thing that was on the magazine aisle in my grocery store was Redbook and the National Enquirer. That’s just what was available to me, so it just felt completely not approachable. I didn’t even dream that.


Jenna Lyons:

I also didn’t really understand what those people did. I didn’t know what a magazine editor did. I did know that I enjoyed making things with my hands and I liked the process of thinking about something, making it and then wearing it and having feedback. That loop for me was really healthy, and so I felt more drawn to that, but I still don’t totally know what goes on in all the magazines.


Debbie Millman:

I understand that a drawing class and learning about Antonio Lopez is what inspired your decision to apply to Parsons School of Design for fashion.


Jenna Lyons:

Yes. My mother was really incredible. She got me a private sewing lessons so that I could really learn to make things outside of my home ec class. I was enrolled in private drawing lessons with this woman named Mrs. Webster, and Mrs. Webster gave me a book called Antonio’s Girls by Antonio Lopez. It was probably one of the most eye-opening things for me.


Jenna Lyons:

You know, I grew up in California where beauty was “Baywatch.” It was blonde hair, blue eyes, big boobs, surfer. That was the only aesthetic that really existed. I open up the pages of Antonio’s Girls and there is Jerry Hall who, granted, she was blonde, but really didn’t have any boobs to speak of; Grace Jones, beautiful, dark skinned, strong black woman; Tina Chow, Asian woman with bright red lips and kind of boyish way of dressing. Just completely different.


Jenna Lyons:

Marisa Berenson with big locks of curly hair. … You know, it was just, I realized that there was another type of beauty out there. The way that he photographed them was not like what I was seeing in the magazines. It wasn’t polished and perfect. They were beautiful but they were free and sexy. I was just completely taken in and it really just got me. I was like, I want to go to New York. I want to be wherever this person is. Wherever this idea of beauty is, I want to go.


Debbie Millman:

So, you moved to New York City in the late 1980s. What a great time to be in Manhattan. What was that like for you going from Southern California to New York City and—


Jenna Lyons:

I always got the chills. First, it was a different place. I mean, this was well before all of the zoning laws have kicked in. You had just clubs, all kinds of clubs everywhere. Underground clubs, dancing clubs, sex clubs. It was just like the wild, wild West but it was amazing. It had that grit. The Meatpacking District was the meatpacking district and there were clubs.


Debbie Millman:

Remember Western Beef?


Jenna Lyons:

Oh, god, are you kidding? I mean, we would hang out—


Debbie Millman:

And the [inaudible] place across that you’d go to at like 4 in the morning?


Jenna Lyons:

Yeah. I remember walking from Nell’s on 14th Street over to [inaudible] and literally, with all the dudes at 4 in the morning, with the meat hanging on the racks. It was just a totally different vibe. But on top of that, it was the first time I’d ever really felt pretty in the way where I could be myself, where I didn’t feel like I was … I had moved here very tan with bleached blonde hair and dressed kind of sexy, like California sexy. When I moved here, nobody dressed like that. It was much more sophisticated. Women with like slicked-back hair. I’d never seen a red lip like that before. You know, sexy was not showing everything. Sexy was understated. It was very different, and I was beyond excited. It was just one of the best. I mean, those early years while I was dirt poor, I have the best memories.


Debbie Millman:

You interned at Donna Karan during your senior year. You said that the clothes were all incredibly beautiful but insanely expensive and you didn’t know anyone who could afford them. It was at that point that you went from wanting to make beautiful clothes to wanting to make things that anyone could afford, and anyone could wear. At that point, did you think that you could do both?


Jenna Lyons:

I think I wanted to believe that. I mean, I was aware of other brands that my friends could buy. My friends could buy Ralph Lauren. My friends could buy J.Crew. My friends could buy, you know, Ann Taylor was very, very different back then.


Debbie Millman:

Yes. There were some great pencil skirts back then.


Jenna Lyons:

Yeah. I wanted to believe that. I knew that where I got my satisfaction and where I got my emotional fuel was through the process of making things for other people. It wasn’t just like I want to make a beautiful thing and very rare three people can afford this $2,500 cashmere jacket. While it is absolutely stunning and I want to live in it and I want to own it, there not that many people that can have that. It didn’t work for me, like emotionally work for me.


Debbie Millman:

You saw a posting on the Parsons job board for a job at J.Crew. At the time, J.Crew was selling a mix of khakis and rugby shirts and inexpensive cardigans. What made you decide to apply there?


Jenna Lyons:

This was exactly the same time that they were starting to shoot on Christy Turlington, Linda Evangelista. They were really making an effort to make really simple, straightforward clothing more elevated. That was Emily Woods. That was her brainchild. She really was trying to shift to thinking around like why shouldn’t an everyday T-shirt be gorgeous and sexy, because it is? I think she was looking at the work of the [inaudible], Avedon’s and Bruce Weber’s, who were able to make something really simple very, very sexy. Not just sexy, but also just chic.


Jenna Lyons:

That was what was really inspiring to me, was to see these models that I knew were walking the runways of Valentino and Prada and Gucci. These high-end models but then they were coming in and being paid to wear a beautiful simple T-shirt, and a sweatshirt, and a pair of leggings, and it looked chic. That was really inspiring to me and made me want that, because it did both in my mind.


Debbie Millman:

There wasn’t actually a job when you interviewed despite the job board ad, but the head of recruiting asked if she could have Xerox copies of your portfolio.


Jenna Lyons:

Well, there wasn’t a job in women’s.


Debbie Millman:

Oh, I see.


Jenna Lyons:

They had a job in men’s, but I had never done men’s, but I figured I would just go and say hi. I also was like, “Well, maybe I could try.”


Jenna Lyons:

Yes … the head of HR at the time, I still remember her. She said, “You don’t have any men’s in your portfolio.” I was like, “I know. I just figured I’d come. You never know if there’s something in the future. So, yeah, she Xeroxes my portfolio and she sent them to Emily Woods, who was living in California at the time. That night, she called me right back. Yeah, I had a very quick interview process. I flew out to L.A., met Emily and did a project. I mean, I’m shortening this but, yeah, I got the job.


Debbie Millman:

She asked you to create eight sketches for Emily Woods.


Jenna Lyons:

Oh, you know all of it.


Debbie Millman:

This is such a great part. You’re asked to make something from nothing for a company you’ve never worked for, then you do.


Jenna Lyons:

I made a booklet of men’s clothes. I had never really sketched men, so I had to learn how to sketch a male figure too, which was … I know that sounds crazy, but it’s a different thing. I’ve been sketching women, and the way that you sketch women, particularly at Parsons, there was like a rhythm to it. My hand-eye coordination, I kept making the men really tall and skinny and it looked so not manly. It was very funny. It took me a while.


Jenna Lyons:

So, yeah, I made eight men’s ideas for sketches. They sent them to Emily and then they hired me. I worked in men’s for about two weeks and then they were just like, “We’re just going to move you over to women’s because this is silly.” And, yeah, I sort of never left.


Debbie Millman:

You started as an assistant to an assistant to someone else’s assistant.


Jenna Lyons:

Yeah, basically. Just for the record, I sat where there was no desk. It was like a weird sort of hallway area and there was no real desk. It was pretty funny. This was early, early days.


Debbie Millman:

What was it like to first start seeing people wear something you designed?


Jenna Lyons:

It’s interesting. The first time it happened, it felt the same the 700th time it happened. It’s so, I don’t know, so exciting. It doesn’t matter if it’s a rugby shirt or a pair of khakis. Like there’s some weird sense of pride that someone parted with their hard-earned money and they liked something that you touched enough to purchase it, and then put it on their body. That’s just amazing. It’s an incredible reflection. It’s really powerful. I know it sounds silly, but it worked for me.


Debbie Millman:

Were you making your own clothes at the time?


Jenna Lyons:

No. I was working a lot. The company was still very young, and it had a very kind of mom-and-pop attitude. I was really excited and into it. I worked till 10 at night. You also have to remember, this was before computers, so we were sending faxes, handwriting longform faxes every night, communicating with the factories about what we wanted to tweak or change on a garment. The process of making clothes at that point was actually really laden with kind of busywork and memos. It was really hard. All of the sketching and stuff was done in the evening hours, writing memos about what kind of button I was looking [for]. I was just on phone calls with button vendors. It was a very different world.


Debbie Millman:

By 2011, you said that you and your colleagues were lost soldiers working away, following orders, and you were shellshocked and burned out from what was going on. What were you imagining your future would be at that point at J.Crew at that time?


Jenna Lyons:

The dates might be little bit off, but it was really right before Mickey Drexler came in. It’s really hard to put into words, but before Mickey joined, I had literally been through three complete line redos. It was exhausting. We had someone, a woman named Jean Jackson, who had been brought in by our parent company who owned us, who would want her to help and consult, so I was sort of following her direction. Then, we had a CEO who had not come from apparel, who really didn’t understand fabric. He was a lovely man, but just did not have the background for it. And then he was gone. Then this other man came in. He stayed for six months, but in that six months, we did a total redirect.


Jenna Lyons:

The trickiest part was I don’t know if I believed in what I was doing, but you get into this weird situation where in order to keep my team, I needed to hold it together and I needed to try and motivate them. So, I had to drink the Kool Aid and really try to push through particularly when they’re coming to me and saying, “I want to leave. I don’t want to be here,” and I’m like, “Please, stick it out.” They’re like, “Are you going to stay?” It was like, oh god, I wanted to go too, but I didn’t want to lie to them. So then, you get in this weird conundrum where you’re promising people you’ll stay but you really don’t want to, so now you have to get up every morning and go into a job that you don’t feel passionate about, that you’re confused and really … it was just a really, really dark time.


Jenna Lyons:

And then Mickey joined, and I thought, “I don’t know if I can do this again.” I just was really … also, what is missing in that little intersection is that it was the first time I was the boss. So, when Jean Jackson came in, they had fired my boss who was my dear friend and mentor. I didn’t have those managerial skills. I wasn’t competent in that way. I have a really distinct memory of someone saying to me—I just inherited this entire team, they were now reporting to me, I had known them maybe for … I had known the senior people who’ve been reporting to me, but I didn’t know all of their team—“Are you telling me this person on the org chart is opaque to you?” I’m like, “Well, they’re not translucent. I don’t know everyone yet.” It was just getting hammered constantly.


Debbie Millman:

You had so many choices that you could have made with your life, but you really were determined to stay loyal to your team, which I think says quite a lot about a person.


Jenna Lyons:

Oh, I think it was that. It was also, just to be fully transparent, I also don’t think my choices … J.Crew was not on the map. No one was excited about J.Crew at the time, nor myself. I remember going to parties and people would ask me what I did, and I would kind of wince and just say I work in fashion and then kind of brush over it. I wasn’t proud at that time because I didn’t feel good about what we were making and what we’re creating and the way that we looked. So, it wasn’t like I had a ton of options, it was just this weird kind of spiral.


Jenna Lyons:

When Mickey came in, like literally day three, it was like a fucking Hail Mary. He was the most exciting. It was the most exciting time of my life because everything that I wanted, he wanted. He wanted to bring back the beauty, he wanted to bring back Italian cashmere, he wanted to bring back the beautiful washed clothes that we had made and get rid of all the stretch things that have been put in, he wanted to get rid of all the slick stuff. He wanted to do real quality work where he wanted to raise the quality of the catalog and the look and the feel. Everything. I was like, “Oh, my god, this is going to be amazing.” All of that darkness really lifted very quickly.


Debbie Millman:

Your partnership marked the end of product design being dictated by corporate strategy at J.Crew and you ended up having to go about redesigning the entire aesthetic of the company. How do you go about doing that? Where do you start in that kind of endeavor?


Jenna Lyons:

First of all, it doesn’t happen overnight. I think if you really went back and looked at the trajectory over time, it did not. We were turning the Titanic and it was not fast. It took multiple seasons to really get our footing, but I do think in terms of how, I mean, I don’t know. You just, again, it was … listen, I can say I could not have done it if I wasn’t excited. I had already redesigned the line three times in the previous year and a half and that is massive, and the team was exhausted. But when you get a group of designers that are able to create things that they’re excited about, no one could stop. We couldn’t wait to get on the plane, couldn’t wait to go to Hong Kong and meet with our factories, couldn’t wait to go to fabric shows. We just couldn’t wait.


Jenna Lyons:

It’s so motivating and I think people really underestimate the power of what creative teams can do when they are excited and engaged and ignited. And I think, you said it, when you’re designing best strategy, it’s not exciting. It doesn’t yield the best results. Mickey just literally took all of that way. He separated the design team from any of that and he said, “Go and do what you love and then let’s talk.” And then he looked to the garments and said, “OK, now let’s see. Well, what do we think they should be priced at? What do we …” We used to work into a price point, and that’s very hard. It was so liberating. It’s hard to say how. We were like really gassed up. It was great.


Debbie Millman:

I read this about the sense of design at the time. There was no Kardashian-level contouring, no overt sexiness, no sense of trying too hard; sleeves were rolled up, shirts half tucked, wide-legged denim paired with leopard-print heels and sequined jackets worn with army green pants. What was the inspiration for the aesthetic that you were creating?


Jenna Lyons:

I think it was rooted in the brand heritage and also just being a magpie. I have a deep attachment to sparkly things, still do. The brand heritage was really this very classic clothing. But I’d also grown up in California and my grandmother used to send me really preppy clothes from Bergdorf Goodman because she lived here in the East Coast. I would remember getting a navy-blue blazer and like a kilt. I remember wearing that navy blazer the first day of school in eighth grade and I think it was, I don’t know, maybe 92 degrees, sweating bullets, but wearing that. I paired that with my T-shirt from The Cure and my dolphin shorts.


Jenna Lyons:

I was used to a mashup because it’s just the way I grew up, and all of my clothes were. I liked that mix of things and I think everyone that I was working with, the stylists were a huge part of that. And the designers really loved that mashup too. There was a sense of ease to things. We all wanted things to be a little messy. We had a similar vibe, so it was very much like an iteration. It was constant vibration off of other people.


Jenna Lyons:

You know, the team, the design team, the styling team, we used to have dress up days, and everyone would dress in stripes, or everyone would dress in winter, or everyone would dress in camel, or everyone will be dressed in khaki. It’s inspiring because when you give a constraint to a designer or a creative person, that’s when they actually get crazy because then they can’t think about anything else other than how they turn that one thing into magic. That’s alchemy. It was so fun and really, really inspiring.


Debbie Millman:

You said that you felt a huge drive to make clothes that everybody could have because of how you felt ostracized by the world of beauty and fashion. Did you ever imagine that the first lady of the United States and her children would be wearing your clothes at President Obama’s inauguration?


Jenna Lyons:

No. Not in a million years. I mean, still I have to pinch myself. I still miss … everything about them. It was such an incredibly inspiring time not just because they were wearing our clothes, obviously, but because they were a couple of really huge makers. Obviously, it was the first time our country actually voted to put a Black man in office. That’s incredible. It felt so hopeful to me. It felt so exciting.


Jenna Lyons:

On top of that, they were so real and connected. They did everything differently than what the past presidencies and first ladies had done. They connected with people. I think that’s what was so incredible, when Michelle Obama went on to “The Jay Leno Show” and said, “I’m wearing J.Crew.” That was a way of connecting with people. She was trying to say, “I’m just like you,” and she did. I think that really resonated with people from a brand perspective but also from a personal perspective. It was so exciting. And then on top of that, in his inaugural speech he talked about gay marriage. That’s the first time a president had publicly acknowledged that it was even a thing. They just felt really, really hopeful.


Debbie Millman:

There was something about and something that’s still really unique and special about Michelle Obama’s fashion style. When she was in office, there was a blog that was recording every single thing that she was wearing.


Jenna Lyons:

Oh, yeah.


Debbie Millman:

And I would go to it every single day.


Jenna Lyons:

Me too.


Debbie Millman:

And then the book came out. There was something so, and I’m still so dazzled by her sartorial choices and the way she combines things.


Jenna Lyons:

Completely.


Debbie Millman:

Everything was so beautifully done, and it looked so effortless. I can’t imagine that it was, but it seemed.


Jenna Lyons:

I know she had some very talented people working with her. Obviously, Ikram Goldman, who has a store in Chicago, she was behind that, and Meredith Koop who I think was also really helping to make sure that she had access to things. But again, she took choices like no one I’ve ever seen. What I’ve really loved is seeing her post-presidency, because watching her, the outfits are to die for. I love—


Debbie Millman:

I know.


Jenna Lyons:

I mean, the thigh-high gold boots and the … I can’t. I die every time. I’m so in love.


Debbie Millman:

In 2008, you became executive creative director at J.Crew. In 2010, you became president of the company. I read that the decision for you to take over as president was a two-second conversation with Mickey Drexler. Is that true?


Jenna Lyons:

He is very decisive. Just to be clear, and I think I want to clarify this for some people because I realized that it does get confusing. I was president and executive creative director of J.Crew Group, which is J.Crew, Madewell and J.Crew Factory. It was all three of those brands, so the scope of the project was pretty massive. I think I get sort of separated and put only into one bucket. It’s hard to imagine just how intense the job was but I think it gives context.


Jenna Lyons:

I think the conversation with Mickey was only two seconds because there wasn’t much to say. I mean, I think he had been gearing up to it. Mickey is very transparent, and he is clear about what he likes and what he does not like. In meetings, he would reference or defer. He would include me on things that I hadn’t been included on before. It was becoming apparent, I think, to not just myself but other people around me that that was where things were going, so when it happened, I remember walking out of the room sort of shellshocked. I hadn’t really prepared for it and I never expected it to happen. And then when it happened, I couldn’t really process it. It was a little overwhelming. It wasn’t what I had ever expected for myself nor dreamed of.


Debbie Millman:

You helped the company tripled its revenue from $690 million in 2003 to $2 billion in 2011. In 2013, The New York Times wrote an article about you with the headline, “The Woman Who Dresses America,” but The New York Post also wrote a piece, nasty, snarky piece, titled “Too Big for Your Britches.” How hard was it to balance how the media was measuring you and how you were measuring yourself?


Jenna Lyons:

Oh, god. I remember listening to Barack Obama actually talk about this. He was like, “Listen, I don’t read the press. I rely on my team to tell me what’s important and what’s happening, if there’s something I should know about, good or bad.” I know that, obviously, I was nowhere near as big as him, but I decided not to read things, and I stopped. The reason was, and his perspective, and I believe this is if you believe all the good, then you have to believe all the bad. The fact of the matter is, I know the truth. I know what’s really going on. I got credit for things I didn’t deserve credit for, I got slammed for things I probably didn’t deserve to get slammed for. And so, I think you have to just take the good with the bad and realize that it’s going to happen no matter how hard you tried. I did the best I could to be as polished with the press as possible, but I stepped in mud many times, sometimes by my own doing, sometimes just because that’s what happened.


Jenna Lyons:

I think once you put your name out there and once you put yourself out there, you are susceptible. It comes with the territory.


Debbie Millman:

You and your then-husband split up around this time and you fell in love with a woman. What was it like to have everything you wore, everything you did, even your relationship and your then-husband, under such scrutiny?


Jenna Lyons:

It’s hard. You get in your head too much. I think the main thing I remember being the most challenging thing was that I would go from, and I know it sounds crazy, but literally having an incredible weekend being at the White House, dancing with the president and the First Lady, singing Stevie Wonder and Beyoncé, things that I never in a million years imagine would happen to me, and then come Monday morning, I’m sitting on the floor with someone who’s three years out of college negotiating about keeping a style on the line. It was a very hard balance. I did my best, but I know … it was confusing. It was emotionally confusing.


Jenna Lyons:

On top of that, it’s not the best thing for a relationship to have such kind of imbalance where I didn’t want to leave the house without putting on makeup. I was concerned about every little thing because I felt like I was under scrutiny. I lived down the street from a very popular hotel and so there are paparazzi there all the time. And so, because I happen to live here, they’re not there for me but they see me. I will be walking my dog, or getting groceries or coming back. It was a lot. I’ve embraced and really enjoyed the past couple of years of being quiet and not being out there in the limelight.


Debbie Millman:

Was it difficult to come out later in life so publicly? I didn’t come out till I was 50, so I can relate to the sudden change in how people view you.


Jenna Lyons:

I know, I know. I know a little bit. I know about your story too.


Jenna Lyons:

Well, first of all it wasn’t my choice, and the Post outed me. I got a call. I remember distinctly being in a meeting and I got paged over the intercom. There’s an intercom at J.Crew. It was Mickey Drexler and Margot Fooshee, who was the head of PR and marketing and the time. All I heard was, “We just got a call from The New York Post. They’re running a story that you are seeing a woman. Should we confirm or deny?” My heart was literally like ba-bump, ba-bump. I can feel it. I was facing the wall and I just heard my voice go, “Confirm.” There was silence in the other end. I don’t think they know what to say. They were just like, “OK. I think we need to talk.” I was like, “OK.” And so, I sat at Mickey’s office with the head of HR, the PR and then we talked and decided what to do.


Jenna Lyons:

I will say, I was treated with so much understanding and respect and acceptance. That was really incredible because I think had that not happened, while it was really challenging, I think it would’ve been much, much harder. I’m deeply grateful for everyone who helped me in that moment because it was really terrifying. I had not told my mother, I had not told my ex-husband, I had not told my son, I had not told my friends, I had not told my family. It was very new. This person had been my friend and we were barely in, and I think we … it was so, so new. I didn’t really know what was happening. So, yeah, it did make it so that I didn’t have to come out.


Debbie Millman:

You know, it’s interesting. It’s not even just the switching teams. I think it’s also just the letting everybody know in your life that’s important to you so that they feel included in something that’s happening. I had a friend that got very angry with me; she found out that I told my cousin before I told her. It’s like just that sense of people wanting to feel like they’re part of what’s happening and not left out.


Jenna Lyons:

Oh, completely. And having their own experience around it. I literally made frantic phone calls. It was 4 o’clock in the afternoon when we got the call. It was going live at midnight. Particularly at that time, anything with my name on it got picked up, so I knew it would get out there quickly. Also, president of a big American brand. My name and face is attached to the company, I had recently separated from my husband. It was juicy. They knew it was going to be interesting. The most bizarre experience was the looks that I got standing outside, picking up my son at school. That was interesting.


Debbie Millman:

Well, know that there were millions of gay women all over the world cheering for you—


Jenna Lyons:

Oh, thank you.


Debbie Millman:

… and still are.


Jenna Lyons:

Thank you. Thank you.


Debbie Millman:

In 2017, after 27 years, you decided to leave J.Crew. I read that you actually wished you’d left a few years earlier. How come?


Jenna Lyons:

I think I had become less effective. I think that there were a lot of things happening within the company that I think were probably what needed to happen, but they didn’t totally align with my desires and my motivation and my enthusiasm. I also think I had closed myself off to other opportunities, and I think that there probably would have been some other things that could have happened. But, listen, hindsight is 2020. It happened when it happened, and it probably happened the way it needed to. I think I talked myself out. I think it had run its course. It used to feel really innate and it used to feel really like I knew exactly what I wanted and felt charged about how to get the best thing and how to push through, and then it just started to shift. It was harder.


Debbie Millman:

Shortly after you left J.Crew, you and the woman that you were outed with by The New York Postalso broke up.


Jenna Lyons:

Yeah.


Debbie Millman:

Jenna, what a shitty year. Could 2017 be any worse for you?


Jenna Lyons:

Listen. I think it was that. It was also, you have to remember it too, I went from having … you know, I had a full-time assistant and then I have a second assistant who took care of everything for me. I had a PR team that also fielded any kind of press calls. I also had a full-time nanny. I went from that to nothing. I didn’t need the nanny anymore because I’m home. I lose my girlfriend. I don’t have anybody helping me. I don’t know how to use an Excel document. My whole life just kind of … I had to take back all of my … my assistant was managing all of my finances with my financial team, but really communicating with them, I hadn’t exercised those muscles in so long and it was scary. I was depressed. It sucked. Damn.


Debbie Millman:

You initially imagined that your next role might be at a big fashion house, but your phone didn’t ring. The entire year after you left was even tougher than you expected. How did you manage? How did you get through it all?


Jenna Lyons:

Please understand, I don’t think I’d managed. I think I literally just like … it’s hard to explain. I left the job. I knew it was time to leave the job. It was my choice, but I really didn’t expect what happened afterwards. And then, on top of that, the partner thing and everything. I didn’t do much. I just put one foot in front of the other. I was really quiet. I was really, really quiet. I would sit on my couch and flip through magazines, look at books, but I don’t know if I retained anything. It was strange. I barely remember some of it. I would think I was really depressed, and I probably didn’t handle it that well, so I wouldn’t use me as a guide.


Debbie Millman:

Well, I think it sounds like you were trying to reacquaint yourself with yourself. I mean, I left a big company. I was president of a design company for 21 years and left. I also feel like I left several years after I should have, but a former partner of mine at another business had said, “Don’t leave cold turkey because you’re going to lose every sense of who you are. Leave slowly and let yourself sort of acquaint with the rest of the world.” I did that, and then I think I did it for too long and so then, by the time, it was just like get the fuck out.


Debbie Millman:

I also experienced that even just going from three days a week to then one day a week, just sort of re-inventing the threads of your being. Everything that you are, the way you understand power, the way you understand identity, the way you understand your place in things and whether you have a place or if it was your job that got you the place. It’s so—


Jenna Lyons:

I am.


Debbie Millman:

… ego toppling.


Jenna Lyons:

For sure. I will say, I don’t think that I actually started to build any of that back in any concrete way until I started to get back into the world. I think the year that I was quiet, I had no sense of how I was going to fit in or where I stood in the whole ecosystem of the fashion industry, of the beauty industry, of the business industry at large. I feel really, really grateful that I had time to figure it out and that I took the time to figure it out.


Jenna Lyons:

I didn’t seek out employment in the beginning because I was really just wanting some time off. And then now, in retrospect, I’m really happy that I didn’t, and I’m sort of happy that no one called. I think I needed a reset. I needed that. It’s funny because I think a lot of people were like, “Oh, did it hurt your feelings? Did it feel like a real ego blow?” Truthfully, I was the one who was like, “no one’s going to call and I know it.” I just knew in my heart that there was going to be a big shift in my life. And it happened.


Debbie Millman:

Do you think that people just felt that whatever they were offering wasn’t worthy of you, or do you feel that it was because you were associated so strongly with one brand? Why did you feel so strongly? Because I never would have predicted that.


Jenna Lyons:

I think probably a combination of the things you just said. I think a couple things—people expect executives to be locked up. And while I was locked up, I wasn’t locked up for that long, and certainly there’s no reason to not start conversations.


Debbie Millman:

Let me just make one thing clear for my listeners. When Jenna says “locked up,” she doesn’t meet in jail. She means with a non-compete.


Jenna Lyons:

Thank you for the clarification. Sorry.


Debbie Millman:

High-powered executives don’t always go to jail when they leave the big company.


Jenna Lyons:

Nope, they don’t. Definitely not. Some of them definitely should. I don’t think I fit in that category.


Jenna Lyons:

So, it may be assumed that I was under contract of some sort in addition, as you mentioned, particularly for a fashion brand, like I’m not going to go to Ralph Lauren or Michael Kors because those names have names on the door and I had my name. I was almost too well known in that way, and who knows if they would have wanted me anyway. I’m not saying that I could have gone there, I’m just saying that the American companies that were available to me, there weren’t a lot. Then there was the Ann Taylor and Banana Republic, and neither one of those were really the right thing. It’s just sort of another version of what I’d just done. It didn’t really feel like … so, there weren’t that many options in that regard. And then, maybe people just didn’t assume that I could do something else. I don’t know. I think it was a combination of all of those things.


Jenna Lyons:

I would have loved to try my hand at Ralph Lauren. It was my dream. I had told Anna Wintour. But Ralph is still there. There’s a team and they’re amazing. It was more of a fantasy than anything else.


Debbie Millman:

Well, now it seems you have several chapters unfurling simultaneously.


Jenna Lyons:

Yes.


Debbie Millman:

You’re the executive producer and star of the show “Stylish with Jenna Lyons” on HBO Max, which is so good.


Jenna Lyons:

Thank you.


Debbie Millman:

I’m so invested in the people that you had been testing to hire.


Jenna Lyons:

Thank you.


Debbie Millman:

I think you made the right decision.


Jenna Lyons:

Thank you.


Debbie Millman:

It’s just so exciting to see what you’re doing. You started a bespoke false eyelash company, which I’ve also bought eyelashes from now. You’re working on the design of a hotel chain and opening pop-up stores. You’ve called your new company Lyons Life After Death. L.A.D.


Jenna Lyons:

Yes.


Debbie Millman:

So, is there any other backstory other than coming back to life with the name?


Jenna Lyons:

Yeah. It’s interesting. There’s been a little bit of a shift in all of that, but I think when I first started, I realized I was taking on quite a few projects. I had this hotel project. Just to be clear, it’s not a chain of hotels. It’s a one-boutique hotel in the Bahamas in Elbow Cay, just to be clear.


Debbie Millman:

OK.


Jenna Lyons:

I don’t want anybody to think that there’s going to be more of them, because then I can’t do other ones. So, if somebody has another one—


Debbie Millman:

It’s true.


Jenna Lyons:

I’m for sale. I’m for hire. So, when I was doing all these different projects, I realized that I had all these things coming in and I was paying people out of my bank account. I sat down with my accountant and he’s like, “You need to have some sort of hub.” So, I created Lyons LAD as a way for me to have a hub and be able to actually pay people out of that.


Jenna Lyons:

As things have gotten bigger, I’ve been looking into a sort of a design consultancy company, which we’ve been calling Sort of Creative. Sort of Creative Agency. The reason is, we make this joke that we’re like, “Well, that’s sort of creative. Is that creative or is it sort of creative?” The reason is because they are now these new people in the mix and it’s not just me, so I wanted to sort of remove it. So, Lyons LAD is the original, and now we’re going to do Sort of Creative Agency.


Jenna Lyons:

I have other projects brewing. I’m working on a furniture line with Roll & Hill. So, there’s that. I’m also consulting with Rockefeller Center, who is working on reinvigorating Rockefeller Center and all of the retail and food and beverage, and just the look and feel. That’s been incredibly fun and really exciting. So, yeah, there’s a lot going on.


Debbie Millman:

Your television show is really wonderful.


Jenna Lyons:

Thank you.


Debbie Millman:

In 2014, you played a Conde Nast editor in a three-episode arc on season three of Girls.


Jenna Lyons:

Yes.


Debbie Millman:

But other than that, you had no experience in television. What has it been like learning something entirely new?


Jenna Lyons:

Harrowing? I am grateful that at my age I get to learn a new trade like that. It’s pretty incredible, and to be able to do it at an executive producer level. The particular challenge though is as I had never done it before, I had no idea how to move the needle on things. I didn’t know what levers to pull, I didn’t know the order things needed to be done. I made so many mistakes just in terms of the way that I thought about how it would get done. I just didn’t understand. I’ve learned a ton, but it was probably one of the hardest and also most rewarding and fun things I’ve had the chance to work on.


Jenna Lyons:

Being in front of the camera, not so fun, really hard. The number of times I went to the bathroom with my mic on. I’m like, “Why am I so hot?” I’m like, “Oh, I have a microphone on my back,” and then I realized I’m sitting on the toilet. Or like having a conversation in the corner, talking to somebody and you’re like, “Wa, wa, wa, wa” and you realized that everyone can hear you. It’s very like invasive. They were in my home, they were in my office, they were in my underwear drawer. It was a lot.


Debbie Millman:

You were involved in literally everything, from the graphics to the music to the editing to the color. I know you experimented with 54 names before landing on Stylish.


Jenna Lyons:

Yes. Yes.


Debbie Millman:

The show is sort of a mix of both—I described it before as a reality TV show, but it’s really kind of a reality TV show and a documentary.


Jenna Lyons:

Yeah.


Debbie Millman:

Why this hybrid approach?


Jenna Lyons:

I think mostly because I wasn’t comfortable doing a reality show based on the way reality shows were being put out there at the time. And so, when I originally spoke with the network, it was really important to me that I wanted it to be reality, meaning wanting it to feel real and not with quotes.


Debbie Millman:

Well, it’s a wonderful show.


Jenna Lyons:

Thank you.


Debbie Millman:

I’m not a reality TV person. When Roxane realized that it was reality TV, she was so excited because I generally don’t want to watch reality TV show with her. She’s like, “We can watch this together.” She loved it too. We’re rooting for different people.


Jenna Lyons:

Thank you.


Debbie Millman:

You were supposed to tape 10 shows, but because of COVID the show ended up eight episodes—


Jenna Lyons:

Correct.


Debbie Millman:

… and filmed the last one in the middle of the pandemic with masks and social distancing, trying to do a pop-up store. How hard was that? I mean, talk about challenges.


Jenna Lyons:

I related the year 2020 to like business twister. I felt like I was constantly trying to put my hand on the blue dot with my right leg twisted underneath me to the green dot and my other hand had is on the … it just was really, there’s nothing about the way that I’m used to working that is connected to distance and COVID. It was just the most incredibly challenging. When we shot the last episode, it was so incredibly hard, not to mention the fact that it was like 100 degrees every day we were shooting and we just happened to pick the final week of filming to be the most excruciating week of the year. I was just … oh, my god. I still can’t believe it actually happened.


Jenna Lyons:

And then … we’re getting ready to launch a business. LoveSeen was literally percolating and coming. Everything collided at once because originally the show was supposed to launch in May, then it got pushed to June, July, August, September. And then we were trying to launch this lash business. LoveSeen launched in September and then the show ended up launching after. It was messy, messy, messy.


Debbie Millman:

You also sold the house in the process.


Jenna Lyons:

Oh, there’s that. Yes, one of the projects for the show was redoing a house. My ex-girlfriend, we still owned a house together in upstate New York. We had had a leak from a broken shower valve. It had been a really slow leak, so we didn’t realize. It collapsed the roof and ruined the furniture and ruined the floors. We redid the house as part of the seventh episode and turned around and sold it and also closed out that chapter. We’ve been sharing that house for the last three years. It did not lack emotional fortitude. There were a lot of tears.


Debbie Millman:

When I saw the house, the original before you redid it, I cried. I was like, “Oh, my god. The floor is buckled.”


Jenna Lyons:

It’s really hard. I know, it seems like a thing, and of course it is just a thing and it’s obviously fixable and it’s not a person, but it is amazing how much you attach homes to experiences and life experience. I just felt like the house was representing the relationship in some way, that it kind of fell apart and buckled. I wasn’t really upset about the house. I mean, of course, it was sad to see that, but it was just like, god, I felt like the house was talking to me and I was like, “Oh, I’m sorry.” And then they have cameras watching you. There was that too.


Debbie Millman:

Yeah. Oh, my god.


Jenna Lyons:

I know.


Debbie Millman:

Will the show be coming back for a second season?


Jenna Lyons:

I don’t know. I hope so.


Debbie Millman:

I do too. Let us know.


Jenna Lyons:

I will let you know.


Debbie Millman:

You’ve also launched a new eyelash business. Did you ever consider calling it Stylash? Stylish with Stylash.


Jenna Lyons:

That’s kind of great. I love that. We’ll do an email called Stylash. I think that’s good.


Debbie Millman:

Yes. With your friend Troi Ollivierre. What made you decide to do that? It’s such a unique and unusual thing to do.


Jenna Lyons:

I know. It’s so weird, right? I mean, honestly. It was kind of another weird, happy accident. I don’t have any eyelashes, so I’m obsessed with eyelashes. It’s part of the side effects of my genetic disorder, and so I noticed them in everyone. I noticed all the women at J.Crew coming into the office wearing eyelash extensions. These women didn’t wear any makeup. They were very, very clean. So, I thought it was interesting that they’re getting eyelash extensions. And then, on the flip side, I was watching all of these YouTube videos of these women wearing contour, eight shades of eyeshadow and lip liner, highlighters.


Jenna Lyons:

They would finish themselves and I was like, “Holy shit.” It was like a different person. But then, they would finish with an eyelash, and I thought it was so interesting that two completely opposing concepts of beauty were focusing on eyelashes. I thought, “Wow. Maybe there’s something in between,” because when I looked at the landscape, everything was pretty over the top. I wanted them, I liked them, I loved what they do but the expressions of beauty and also the lashes themselves were pretty bold. I wanted something that was a little different.


Jenna Lyons:

And so, I was having a conversation with my now partners from Magnet and I just, I don’t know, just threw it out there. They got excited, we got excited, and here we are. We’re off to the races. It happened. I mean, launching a business during COVID. Like, please, never again in my life.


Debbie Millman:

But the fact is, for those of us, like me, who love having eyelash extensions but can’t because of COVID, it’s a great, great solve and you can get addicted. You have lots of different styles of lashes. The name of your company is LoveSeen—


Jenna Lyons:

Correct.


Debbie Millman:

… and the names of the lash varieties all have four letters: Cate, Inez, Noor, Troi, Jack, Axel, Levi, Iris, Luca and Romy. I bought Cate because I think that that’s a good lash for a droopy eye like I have due to lashes. So, what do you make of the increase in the business of eyelashes? When do you see that having really taken off? Because now I think it’s reaching a tipping point where it’s become interesting.


Jenna Lyons:

It is amazing. Listen, I think that there has been a dramatic shift in the beauty business at large if you really think about. … The fashion industry as well. It’s really been turned over to the people, so to speak. It’s moved away from the industry pushing down and telling you what you should have. Now, the people are saying “this is what we want,” and the businesses are listening. I think that is pretty remarkable. It’s a massive paradigm shift in business in general. I think, as you see more people doing makeup videos and putting lashes on, there’s a clear understanding, and I think businesses are starting to understand, that there’s all different desires.


Jenna Lyons:

While for the most part you had a pretty, pretty singular look and feel in the beauty industry, the glamor was kind of the same. If you looked at Maybelline, Revlon, CoverGirl, all the big ones, they didn’t look that different. Now, you’re getting Huda Beauty, who is doing total over-the-top glam, and then you’re getting Ilia, which is doing really pared-down clean. You have Glossier, which is literally just sort of kissing yourself with beauty but not really changing yourself. There’s all different ways that people are playing, and I think it’s changed the way that industry has addressed things. The biggest shifts I think are eyelashes for one, and then just the skin foundations. If you look at the world of foundation, it is literally a hundred million times different than it was five years ago. There are so many more options, and I think that’s incredible, and there should be. Ironically, that’s just what we’re trying to do. Eyelashes are pretty much only for people who really wanted big glam and big makeup. What we’re saying is, “OK, well, what about the people that don’t want big glam and big makeup? Still want the kick but don’t really want to do that full expression?”


Jenna Lyons:

I don’t like to wear black eyeliner all the time. I can wear the Luca or the Iris in brown and do a tiny little bit of brown shadow on my lash line. I don’t get that heavier makeup look and I can wear them walking my dog, which I normally do. I love it.


Debbie Millman:

Yeah. I love beauty that is easy.


Jenna Lyons:

Me too.


Debbie Millman:

I love the new brow craze as well—so I can do my brow and I can have a lash and just throw in some lipstick and that’s it.


Jenna Lyons:

Totally.


Debbie Millman:

I still look more put together that I would’ve if I just sort of rolled out of it.


Jenna Lyons:

Totally. Especially in a Zoom call. I really do think about it when I put on the lash. I’ve gotten good at it. The tool has helped tremendously. I know you said that you had a little bit of a hard time.


Debbie Millman:

I’m learning.


Jenna Lyons:

Listen, everyone does. No one gets it right the first time. I have now learned some tricks that have really helped, but the tool makes it much easier. Now I can get them on in two seconds, and I’m like, “Damn, it really does make a difference on my calls.” I’m like, “Oh, snazzy.”


Debbie Millman:

Well, I understand before the pandemic you’d never heard of Zoom. I hadn’t either, actually.


Jenna Lyons:

I hadn’t. I had never been on a Zoom call. I mean, my work is so tactile. You know, it’s interesting, I was talking to the girl from the Crown Affair, they are a brand of haircare. We were texting back and forth because she had posted all these pictures of her getting ready to produce the line. There were all these boards lined up and it’s like, “Oh, god. I’ve never missed a board more in my entire life.” Like, boards with images where you can move things around and pin it over here. I was like, “I don’t want to pin it on the computer. I just don’t want to.”


Debbie Millman:

I want to touch it.


Jenna Lyons:

Me too.


Debbie Millman:

Jenna, I have two last questions for you. The first, I understand Ashley Merriman, the chef at the restaurant Prune, has been cooking for you.


Jenna Lyons:

Yes.


Debbie Millman:

Her wife, Gabrielle Hamilton, was a guest on the show a few months ago. What kinds of things are they making you?


Jenna Lyons:

Oh, my god. I have to say, it is like the saving grace of COVID. I have been eating like a fucking queen. It’s amazing. I mean, there’s this stuff I call crack, which is basically this roasted smoked tomatoes with onions and olive oil. It just goes on anything. It is probably one of the single-best things I’ve ever had in my life. She makes this [inaudible] stew that is to die for. She makes the most incredible white bean salad that I like absolutely, white bean salad and a white bean soup that I love. A French onion soup that is insane, duck breast with … oh, and agrodolce. I didn’t even know what agrodolce was.


Debbie Millman:

I don’t what that is. It sounds good.


Jenna Lyons:

It’s like onion crack. It’s basically all these different onions and then you put them in a pan with a little bit of butter and a little bit of sugar and then they crack. It’s insanity. It goes on everything well. I could go on and on. It’s been the best. She’s incredible. I’m so lucky.


Debbie Millman:

So, my last question is this, and it’s rather silly. I understand that texting has saved the relationship that you have with your mother.


Jenna Lyons:

It’s totally true. I hate to say this—my mom, and she will say this, my mom suffers from Asperger’s, and it’s not as easy for her communication. She just doesn’t always know how to emote and finds it troubling, challenging. We’ve struggled. It’s really interesting, you know, you can change the tone of a text so deeply with a heart emoji, or a crazy face. Now that she’s gotten used to it and understands how to use them, a lot of things that I think would have been said before that have might had fallen flat or might have triggered me into feeling like maybe the way I interpreted it, you know with a simple heart and flower or exclamation point, I have completely changed. It’s really softened our engagement and made it easier for us to connect, and connect more frequently and just be … I don’t know. You know, sharing pictures and liking the things. I know it sounds crazy, but it’s been really, really helpful.


Debbie Millman:

No one would have predicted how popular texting was going to be. There was no future of saying we’re going to all be using emojis in 15 years 15 years ago. But there’s something about the efficiency of it that I think has sort of democratized conversation in a lot of ways.


Jenna Lyons:

You know, I’ll say, “Oh, I miss you. I can’t wait to see you,” in a different, like with a bunch of hearts. It somehow feels different than when you’re on a call with your mom. You’re like, “OK, bye mom.” You don’t take the time because there’s things I’ll say in text that I probably wouldn’t, and she too. My mom made her own emoji. What is it called? What are those things called?


Debbie Millman:

An avatar or a bitmoji?


Jenna Lyons:

Bitmoji, yes. My mom has her own bitmoji. My mom is 88. My mom has got a bitmoji and she sent that thing through. I’m like, “Yes, mom. It’s so great.” I’m so proud of her. I’m like, you go. It’s incredible. I don’t know, that’s the kind of stuff that like, it really does. It helps. It feels like … she’s always been really good at being on top of whatever it is now. Because she was a piano teacher, so she always was around young kids, which I think is really incredible. It’s kept her kind of connected. And now she really tries. She tries very hard, and I really appreciate it. It’s definitely hats off, mom. Nice work.


Debbie Millman:

Jenna Lyons, thank you, thank you, thank you for helping to make the world a more stylish, joyful place.


Jenna Lyons:

Thank you.


Debbie Millman:

And thank you so much for joining me today on Design Matters.


Jenna Lyons:

Thank you. Yeah, I’m so impressed with your research. That was an incredible interview. I really appreciate it, and it was so incredibly—


Debbie Millman:

Oh, thank you.


Jenna Lyons:

… nice. So nice to talk to you.


Debbie Millman:

“Stylish with Jenna Lyons” is currently on HBO Max, and you can read all about her new eyelash line and buy eyelashes for yourself. LoveSeen at loveseen.com.


Debbie Millman:

This is the 17th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.

And remember, we can talk about making a difference, we can make a difference, or we can do both.  — Debbie Millman