“I was surprised there was so much pink available.”
Spouses (above): Casey Legler, author, restaurateur, and former Olympian, and Siri May, senior adviser at the Center for Reproductive Rights
Siri: I was excited to pick out clothes for Casey. We decided because of this story that we should pick out outfits for each other for a date and then just leave them out for each other.
Casey: We have lots of conversations about clothes. Siri collects garments, and we’re both intentional about what we wear. Siri’s style is poetic and has this distinguished elegance to it as well. I loved finding out what she’d picked for me. I was surprised there was so much pink available — surprised and delighted.
“Jane has some notion that I wear color.”
Friends: Dr. Jane Aronson, physician and founder of Worldwide Orphans, and Alexi Ashe Meyers, human-rights lawyer
Jane: This outfit is a little outlandish — kind of dominatrix, which I’m not — but leather is so sexy! I loved how my arms looked in that top, and I loved the feathers. They were ridiculous.
Alexi: Jane has some notion that I wear color. I stick to high-waisted black Levi’s and a big sweater. I love the dress she chose, in theory, but I don’t know how it looked. I met Jane after graduating from law school. She said, “What are you doing next month?” I said, “Nothing,” and she said, “Come to Haiti with me,” which was exactly what I was looking for.
“The fun thing about drag is one night I can wear lingerie and harnesses, another I can be super-princessy.”
Roommates: West Dakota, artist and model, and Dynasty, editorial assistant at the Cut
Dynasty: We met each other through the Brooklyn drag scene a year and a half ago. Anytime we have a performance, we dress each other, borrow from each other. The fun thing about drag is, one night I can wear lingerie and harnesses, another I can be super-princessy. Sometimes I just want to wear a suit.
West Dakota: I love feminine silhouettes, flowy pieces, and long dresses. I thought our outfits looked really good together.
“We often send each other photos of our outfits to get input.”
Co-creators of Brown Girls: Fatimah Asghar, artist, and Sam Bailey, filmmaker
Sam: We met in Chicago seven years ago, in the writing scene, but it wasn’t until creating the series that we got super-close. Since moving to L.A., we go to so many events. We often send each other photos of our outfits to get input. She’s an artist. She loves mixing silhouettes. She’s great with playing with her look, whereas I’m more into menswear and streetwear. Fati picked out something for me that I wouldn’t pick for myself, but I felt sexy and powerful. For her I wanted to play with androgyny, something she never does.
Fatimah: It was cool to see myself through the eyes of someone else. For instance, Sam asked that my hair be slicked back in a way I’d never wear it. She was playing up my normal look and challenging it.
“Most of my clothes look like they’ve had life happen to them.”
Partners: Adele Thibodeaux, writer, and Katja Blichfeld, co-creator of High Maintenance
Katja: We share a lot of clothes and shoes. There’s a lot of, “Are you going to wear the black shoes?” I saw this white suit and was like, “Adele, you have to wear that.” I like clothes that are ungendered. Most of my clothes are used or thrifted and look like they’ve had some life happen to them already.
Adele: Similar to Katja, my style is laid-back. I have a red shirt that I’ve had since before I was out of the closet — it’s just a workman’s shirt that feels really thick. I almost wore it here today.
“I’m all over the place when it comes to fashion.”
Twins: Cipriana Quann, writer, and TK Wonder, model, writer, and musician
TK: Cipriana stopped taking any fashion advice from me when I borrowed a T-shirt from her as a teenager and customized it like an ’80s rocker. I’m all over the place when it comes to my fashion choices, and Cipriana’s style is consistent: ’70s, modernized in her own way. I love it.
Cipriana: The only time we give each other advice is if I come from the bathroom with toilet tissue stuck to my shoe. I never would’ve chosen to pair such bold colors together — but somehow the things she chose were my style. I did add my own accents: the visor and earrings.
“I like when Mommy wears tutus.”
Mother and Daughter: Eva Chen, head of fashion partnerships at Instagram, author of Juno Valentine and the Magical Shoes and A Is for Awesome!, and Ren Bannister, 4-year-old
Eva: Yesterday, Ren said that she was going to dress me in a tutu. She pretty much made a beeline for this Dior dress because it looks like a tutu. I wanted to wear a green Gucci jacket with maybe a pair of jeans — mom jeans — white T-shirt, and sneakers. But she chose a naked ball gown for me. Which is okay.
Ren: I like when Mommy wears tutus. We match. You can dance in a tutu. Dinosaurs don’t dance in tutus. My mommy is mine.
“I’m not going to completely dismantle what it is to be Tonne.”
Mentee and Mentor: Gabriella Karefa-Johnson, style director at Garage, and Tonne Goodman, former fashion editor at Vogue and author of Tonne Goodman: Point of View
Gabriella: I can’t imagine my life without Tonne Goodman — I was her assistant for over three years, traveling the world. It would have been fun to put Tonne in a boxy Balenciaga jacket, but that’s not her, and at the end of the day, I’m not going to completely dismantle what it is to be Tonne.
Tonne: I said to Gabriella the other day, “Does it seem strange to you that you have a good friend who is as old as your mother?” She said no — and it’s the same way I feel about her. I thought the combination of blues and gingham was very chic but had a sort of irreverence that she likes.
“Ryann always leaves with something from my closet — maybe I subconsciously shop for her.”
Hairstylist and Client: Ryann Bosetti, hairstylist, and Amanda Bupp, fashion executive
Ryann: I live in Marfa, Texas, and I met her while she was on vacation there about six years ago. It’s a small town, so when someone like her shows up, you notice them immediately. I’ve been cutting her hair ever since. I was intimidated because Amanda knows what she likes way more than I know what I like. She’s a boss. Powerful, discerning, and intricate. We were laughing because we both picked these real gothy, witchy looks for each other.
Amanda: Ryann’s hair is tousled but always perfect. And she’s just always wearing a high-waisted pant to highlight her legs. When she visits me, she always leaves with something from my closet that I haven’t worn in a while. Maybe I subconsciously shop for her.
“This batwing top gives me a feeling of power.”
Three generations: Doreen Deleon, grandmother; Lisa Deleon, mother; Kai Avent-Deleon, owner of Sincerely, Tommy
Kai: My mom takes a lot of direction from me when it comes to brands. I put her onto Margiela, and she’s become a little obsessed with buying it. She also buys things I can’t really afford, so I can live through her. My grandmother is more dramatic. She’ll go with like a skirt and a billowy blouse that looks like an art piece.
Lisa: They’ve both said to me at times that I should be a bit more daring, wear things that are more fun. I might wear this on a special occasion, but I wouldn’t wear it grocery shopping.
Doreen: I’ve gotten to a stage in my life where I see pointed tips on boots and think, I’m a great grandmother, those are not my boots. This batwing top gives me a feeling of power. When it all came together, I said, “Wow!” It made me feel like the mother of the world.
“I always know what she wants because that’s what I want.”
Sisters: Nadia Gohar, artist, and Laila Gohar, food designer
Nadia: I’d say the shapes in her wardrobe are sometimes more exaggerated than mine, but we share a similar style for everything — even food. I always know what she wants because it’s what I want.
Laila: My sister and I are only 13 months apart. Sometimes I feel like we’re kind of the same person. I chose that outfit for Nadia because that’s one of my favorite colors, and I liked that the shape was boxy but the fabric was really light. For me, she chose a dress that was really tight and short. I was really into it. I always find it interesting when people describe their style as, It’s a little tomboy, it’s a little this, a little that. I’m like, what do you mean? Do you always look like that? I’m always in flux.
*This article appears in the February 4, 2019, issue of New York Magazine. Subscribe Now!
More From The Spring 2019 Fashion Issue
- A Fashion Historian Explains This Season’s Shoes
- This Season’s Monster Blazers Are Part David Byrne, Part Hillary Clinton
- A Trip to the Laundromat With 18 New Yorkers
