“When I left J. Crew, I thought I was going to have a lot of calls and I didn’t. I was terrified that I wouldn’t ever work again—I kind of just took every call that came my way and ended up doing lots of different stuff. It’s all connected to what I was doing before, but the things I’d really worry about, like that the clothes were seasonal and would expire and go on sale after a certain date, I don’t worry about anymore. That part is so great.

CAREER
My first project [post J. Crew] was this hotel in the Bahamas—it was a ground-up build, and I oversaw the look and feel of everything. It’s funny, because a lot of people think that kind of design is so different from what I did in my previous life, but I was overseeing the look of every J. Crew, Madewell, and Factory store by the end of it. After the hotel, I took a phone call from someone who was like, ‘Hey, do you want to do TV?’ I definitely did not, but we talked, and before I knew it I was on a reality show. It’ll be on HBO Max at the end of November, and the whole thing is about transformations—some of them are fashion and beauty, and some of them are home. My ethos is so, so similar whether I’m putting together outfits or decor. With apparel, oftentimes it’s a mix of materials—if I’m wearing a flannel trouser I’d mix it with a crisper shirt and maybe a hint of something sparkly. With home, it’s kind of the same thing. If you have a soft, fluffy rug, maybe the thing that goes on it is a bit crisper; maybe you have a moment of brass.

Separate from all of that was Loveseen. It started because I am obsessed with teeth, skin, and hair—I have a genetic disorder that affects all three of those things, so I notice them in other people. I went on The Oprah Winfrey Show years ago, and before I went out Oprah came backstage to say hello. I don't have any eyebrows and I don't have any eyelashes, and next to her I felt like a wet rag. After she left, my makeup artist Troi Ollivierre put extensions and eyelashes on me. It worked for the show, but I couldn't really wear the lashes that were on the market. They were pretty big and dramatic, and are meant to sit on top of your real lashes. I don’t really have anything for them to sit on, and I don’t have that natural dark lash line that sort of camouflages them. Troi and I developed these eyelashes that can work for me, and can also work if you do have natural eyelashes. If you want to just wear a bare face and a red lip, Loveseen lashes work for that. The most dramatic we go is a longer cat eye, or maybe a playful blue—you don’t need an entire face of bold makeup for them to look right.

MAKEUP
I don’t like to wear a lot of makeup because I’m getting older and when you get more wrinkles, makeup settles into the crevices. It can look heavy. Now I stay away from anything that’s chalky, or dry, or powdery, so I’ve had to change a lot of what I was using. I really like that Blur Stick from Milk, but my favorite makeup product is the Dior Airflash stuff. You’re supposed to spray it onto a sponge but I spray it right on my face. My lungs are probably covered in Neutral 2 but I don’t care—in two seconds, I can walk out the door. The other thing that’s life-changing is microblading. I wear glasses that hide my lack of brows a little, but especially at the pool or the beach, I look a little bit like a burn patient. It’s amazing how hair structures the face. Audrey Glass is the best microblader ever. It’s one thing to be able to fill in or make more of an arch, but it’s another to give someone who has nothing an actual brow shape. She figured out what would look natural on my face and went with the fact my eyes are a little uneven instead of trying to over correct. The microblading lasts about six months, and when it fades it becomes just a halo of color.

Eyelashes, a red lip, and no eyeshadow really works on me. I used to go so close to my eye with eyeshadow that it actually made my eyes look smaller. Particularly with the glasses. If I do wear eyeshadow, one of the tricks I’ve learned is that if I put it up higher on my lid, like above the crease, my eyes look bigger. More often, I do this thing called tightlining on my top lids. I’ve been wearing the eyelashes a lot, especially the Levi and the Jack in Brown, so I know what tightlining is now. The eyeliner I love is this Tom Ford one that has two different ends—I find that it’s clean, stays, and is very easy for me to control. My favorite red lip is Red Square from Nars. An oldie but a goodie, and the texture of it just works on me. Another lip thing I love is this Cle Melting Powder. I use one that looks brown, and then a little bit of the pink one on top of it. Some lip products make my lips so dry that they start to burn, and these don’t. I have a hard time with that.

I don’t really wear highlighters—however, I buy a lot of them. There’s one called Spotlight from Absolute New York that’s very similar to the Cover Fx one, but has better colors. The one that’s so beautiful on everyone is called Bronze Rose. I use that in the inner corners of my eyes. Flesh Beauty has one in a pot I love, there’s also one from Sai, one from Ilia… I love them all. My other favorite things are those Kaja bento boxes. I’m a Cloud Paint devotee and have every color, but the process of banging my cheeks with those heart stamps is so fun. They’re something a 12-year-old would own but I fucking love them.

SKINCARE
The two things I mentioned in my last Top Shelf that I still use are this Arcona Brightening Gommage and P50. But my new favorite thing is Biologique Recherche’s Masque Vernix. I had a facial at Joanna Czech that was kind of life-changing, and she put this stuff on at the end. That night I had to go to an event, and as Troi was doing my makeup, he commented that my skin looked plump which, at my age, nothing is plump. Or, the parts that are plump are not the parts I want to be plump. Ugh. Anyway, on top of that, my skin absorbs makeup quite easily, and this stuff made the makeup stay. It also sort of helped fill in the lines without caking. It’s so expensive, but I will never ever talk something up if it doesn’t really work and this shit is insane. My only complaint is, like all Biologique products, it kind of smells.

My hardcore skincare stuff is really tools. I use one of those prickly dermarollers… Should I not do that? It’s a little bit masochistic, like exercising, but I don’t know if it actually works. I love these freezer sticks, too. Romy Soleimani did my makeup for the SAG awards when I was in LA, and she used these on me. They look like a sex toy—so much so that when my son saw them he was like, ‘Mom, what are you doing?’ But they make me look not dead.

HAIR
I have really thin hair that tends to be frizzy, and I have tried so many different things. If I use the Ouai shampoo and the Le Labo conditioner and go to bed with it wet, it looks perfect when I wake up. The shampoo leaves my hair quite soft, I love the smell of the conditioner and that it’s so thick, and I haven’t found another combination that actually helps with my frizz. I can’t wash my hair that much because it’s thin but also because my grays are so dry.

The gray came in as a streak in the very beginning, and I was like, ‘Yeah! Cool!’ And then the rest of my hair started to go gray, and it was not as cool. I started getting glosses to cover it—I’d lose an entire Saturday sitting in the chair, spend $400, and the color would be gone three days later. So one time my colorist used this stuff to help the hair absorb color. On the day of that appointment, a friend had flown in from California to visit me and I had to leave her my only set of keys. When I came home from the salon, she was supposed to let me in. I got there, rang the doorbell, and my friend came to the door, looked at me, made this weird face and walked away. I rang the doorbell again, and she didn’t come back. I called her and was like, ‘What the fuck?’ She didn’t recognize me—she thought I was some woman handing out pamphlets wearing a wig, because my hair looked like a fucking wig, because it had taken the dye so much that I had zero undulation of color! That was the end of covering my gray.

NAILS + BODY + FRAGRANCE
My nails are either bright orange-red or nothing. I’m really religious about that. I have tried many reds and I keep going back to Russian Roulette, and otherwise it’s a buff. I can do the buff on myself, but Glamsquad just opened again and I just have to say thank God. My toes were not OK—I can barely even touch my toes, much less paint them.

Coffee in general is my favorite thing in life. I love coffee, I love coffee ice cream, and I love this coffee scrub from Le Labo. I give it to a lot of people as gifts. I also used to use baby oil in the shower, but I almost broke my neck once because it gets so slippery. Now I use this oil from Wonder Valley. It doesn’t leave the shower totally greasy, which I love, and the smell is great. Someone got me the first one, but I just ordered a whole case of it.

I know this is going to sound strange, but when I was working at J. Crew, I distinctly remember people saying, ‘I know you’re in the office because I can smell you from the elevator,’ and there was something about that presence that I really liked. I felt like I had to own this big space. Now I wear less perfume, because I’m trying to be a little more contained. I still use Creed Silver Mountain Water, which has been my scent since before the dawn of time. If I’m not wearing it, my son will ask me to put it on—he’s older now, but when he would go to camp I’d spray his pillowcases and blanket with it. Smell can be really comforting, so I wear it every single day.”

—as told to ITG

Jenna Lyons photographed by Alexandra Genova in New York on September 12, 2020