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How I Shop: Willa Bennett

Photo: Hunter Abrams/Courtesy of Highsnobiety

We all buy clothes, but no two people shop the same. It can be a social experience, and a deeply personal one; at times, it can be impulsive and entertaining, at others, purpose-driven, a chore. Where do you shop? When do you shop? How do you decide what you need, how much to spend and what’s “you”? These are some of the questions we’re putting to prominent figures in our column “How I Shop.”

Over the course of our Zoom call, Willa Bennett paces in her office, leans on her desk and shows me the bright blue socks tucked under her auburn suit trousers. She’s wearing the same Bode shirt she was photographed in for a recent feature in the Washington Post. One thing is clear from the jump: The editor-in-chief of Highsnobiety is having fun with her style. 

Photos: Djeneba Aduayom/Courtesy of Highsnobiety

Since taking over the publication in 2022 at the age of 27, Bennett has produced bright and animated covers starring artists like Central Cee, Megan Thee Stallion and New Jeans. The most recent issue, for Spring 2024, spotlights three icons: André 3000, Dries Van Noten and Pamela Anderson. “The focus of this [issue] is this idea of relevance and legacy,” she says.

Outside of her work, the California-born editor has also become known for her distinctly playful uniform, which she’s wearing during our conversation. We talked about her suiting preferences, where she loves to shop, her style icons and more — read on for the highlights. 

Photo: Celeste Sloman for The Washington Post via Getty Images

“I’ve always been interested in oversized suits, not tight clothing. I really don’t like uncomfortable clothing. It’s pretty rare you’ll see me in heels. I’m really about going with what I feel like in the morning and what feels best. I’m obsessed with having a uniform and having the same things I wear. Having too many clothes stresses me out.

“I wear my Prada loafers literally every day. I have pretty much worn these every day for the past three weeks — they came with me to Men’s Fashion Week, Milan, Paris and all through New York Fashion Week. They went with me to the Grammys. They’re really comfortable. 

“I have always felt more comfortable in menswear. I used to always, always, always go to thrift stores with my friends growing up, and I would go to the men’s section first. I would always remove the shoulder pads and make the suit fit the way I wanted. I never really wanted to be a designer, but I was always drawn to this concept that you can change this part of yourself externally. It has always been something I’ve been really interested in. Especially at Highsnobiety, it’s really about how you’re wearing things and why you’re wearing them, versus what you’re wearing.

Kate Berlant, Willa Bennett and Zoey Deutch at the Coach Fall 2023 show

Photo: Lexie Moreland/WWD via Getty Images

“The suit is about it fitting right. I have a tailor that I’m pretty close with, and he’s great at taking a suit — maybe I find one online that I really want but just isn’t made for my body — and helping me move things around. I’m very selective about my suits because I don’t like having too many clothes. I pretty much give the clothes I don’t wear anymore to my siblings.

Prada is one of my favorite brands. I go through phases where I’ll wear something every single day for three weeks, and then I’ll completely never look at it again. I’ve always really liked Dries [Van Noten] — what I love about menswear is it’s so consistent: You’re always going to get some beautiful suiting, beautiful ties and bow ties, some sort of trouser. Dries does all this really well. 

“It’s always about supporting the people closest to you. A designer like Willie Norris… I wrote about Willie in previous positions, and I’ve continued to work with Willie in this position. Dries, I’ve been a longtime fan of. We continue to support him constantly. We carry it in the shop, we support editorially, we’ll obviously be at the show — it’s about building those connections, and for me, they feel really real and not professional. 

Willa Bennett and Connor McKnight at the 2023 CFDA Awards

Photo: Taylor Hill/FilmMagic

Connor McKnight is one of my favorite designers. He was on the cover of Highsnob, and I was wearing him at the Grammys. It really is for me about building that relationship and having the people you really champion. Connor has become like a dear friend of mine. We walked the CFDA Awards carpet. We’re real friends. I’ve been wearing this yellow jacket he gave me constantly. 

“It’s not transactional to me. It’s like, ‘Do I want to wear this brand? Is the product actually good?’ I think that’s also integral to the DNA of Highsnobiety where we actually are looking at products at the end of the day and talking about the quality behind them and why we’re wearing them. If I wouldn’t wear it, I’m not putting it in the magazine.

“I’m in a big Bode phase. I feel like that one’s been really long, though. It’s a forever. ERL… My friend Dae [Lim] runs Sundae School, and I have some of my favorite fleeces from them. I love Beepy Bella — the world she created is both specific and intentional, and all the projects she does build off of that. I wear her hats all the time. 

Celeste Yim and Willa Bennett at a Sundae School event in 2023

BFA/Sansho Scott/Courtesy of Sundae School

“I kind of dress the same on the weekends. I used to wear a lot of Converse growing up. I feel like I haven’t really been wearing them as much in the last couple years, but I still wear my Vans and my Dunks.

“I wear a bunch of necklaces. [There’s one] from an emerging designer I just found on Instagram and bought. It’s a carabiner, and it’s really awesome. I’ve just collected silver chains from different places I’ve traveled. There’s another one of my name in Korean — my partner and their mom got it for me for Christmas.

“[Ties are] such a staple in my personal style. They feel so integral to who I am. I’m not into oversized ties. I will wear skinny ones on special occasions, but I love a classic tie. I have a special Dries tie that I’ve worn a ton. There are some Prada ones and a vintage Missoni tie I’ve had for a while. Ralph Lauren makes incredible ties, and I’ve been wearing vintage Ralph Lauren ties pretty much since I was a teenager. I’ll never get rid of them.

Willa Bennett at a Tag Heur event in 2023

Photo: Craig Barritt/Getty Images

“I love the vintage stores in Paris. I’ve found some of my favorite things there, like this really beautiful vintage Yves Saint Laurent suit that fit perfectly, no tailoring needing. It was like $70. It was this vintage store across from the Supreme store.

“[My first fashion splurge was] this Ralph Lauren suit that I really couldn’t afford. It was vintage, so it wasn’t that expensive. I had just written my first cover story, and I took the couple hundred dollars I got and bought this suit that did not fit me at all. It took me so long before I could get it tailored because I had to wait to write another cover. It was a process. I was so excited to write a cover story and be able to buy a suit with my work… but, in execution, everything went wrong about it.

Billie Eilish, André 3000 and A$AP Rocky [are my style icons], honestly. I have always admired Billie’s style. Rocky wore the ERLs in Highsnobiety, then Billie on ‘SNL’ and then me. Billie has really [honed] in on who she is and what she wears — you could look at how she dressed at the ‘Barbie’ premieres, and it was still her. André 3000 is the style North Star. I don’t think there’s anyone that understands style better than him. As for A$AP Rocky, people on the editorial team have said with their full chest on the internet: He’s the best dressed person alive. 

Willa Bennett at a Kenzo event in 2022

Photo: Arturo Holmes/Getty Images

Sonny Angels are big thing of the Highsnob office right now. We’re all very into collecting them… There’s this Smitski that I have on my desk right now that an intern gave me as a thank you. Apart from that, I buy a lot of vintage. There are a couple of places in the West Village, which aren’t really a secret. 

“[When shopping, I honestly make my partner come with me and listen to me talk the whole time. They’re very nice and just let it go.

“I’m sillier than people realize. I obviously have my uniform staples, but I wear bright blue socks, wild earrings or necklace, headband bows. There are little hints of femininity that I try to express in very specific details. I have fun, and I like experimenting and wearing a ton of patterns. I’ll wear my Sundae School fleece that’s a rainbow with a rainbow shirt under it and a yellow turtleneck and suit pants.” 

This interview has been edited and condensed for clarity.

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