Willa Bennett, editor-in-chief of Cosmopolitan and Seventeen, has worked in the fashion industry her entire career, and has held her current post gleefully for the last seven months. A veteran of GQ and Highsnobiety—she made the Forbes 30 Under 30 list at the former and was editor-in-chief of the latter—she’s no stranger to men’s fashion. “I come from menswear, and I still look at things through a menswear perspective,” she tells me in her office high up at Hearst Tower. One look at her suit-and-tie personal style, and it’s clear she’s not bluffing.
“My style is quite traditional,” she quips. “People are surprised by how classic and traditional I dress, but I really do find structure in that.” She tells me that because she doesn’t have many clothes, she wears her garments very often. Like many successful 30-somethings in the fashion industry, Bennett advises you to buy less and look into quality. “Truly, I will wear this Thom Browne suit that I’m wearing right now 10,000 times.”
Ahead of Cosmopolitan’s newest print issue and the chaos the Met Gala brings to NYC, I sat down with Willa to discuss the lessons she’s learned from working in the industry and their impact on her style, advice for young writers, some of her favorite brands, and plenty more.
Fit One
Tell me about your career. How did you start, and how did you get to your current position today?
I was an intern at Seventeen. It was my first job, and then I worked across Bustle Digital Group. I was at GQ for many years, which is really where I found my voice in menswear and became such and an obsessive menswear consumer. It was a bit of a smaller industry at that time. I came up in the space of really appreciating good tailoring and emerging designers and loving suits and ties. I became really, really obsessed with it there. To be surrounded with so many people who were also just as obsessed was so exciting and unifying. From there I got pushed to be the editor-in-chief of Highsnobiety. There, I basically inherited this more menswear focused brand and, in my time, tried to develop it to be a youth culture platform. In doing that we did broaden it to emerging designers and young people who had a great POV. But I always stayed true to my menswear roots. Billie Eilish was my first cover and she was wearing Simone Rocha and runway Marc Jacobs. Within that, I always had my spin on it, but taste-wise it really broadened me to not just think so myopically about menswear. I’ve been here for seven months.
Fit Two
Has your style changed much from the start of your career to now?
My clothes are nicer.
Aside from your clothes being nicer.
Well, my personal style is the same. I still wear the same things all the time and I still wear suits mainly. I think I care more about the quality in my thirties than I did before. I just don’t buy badly made clothes anymore. The biggest thing that’s changed is I definitely have more hints of femininity in my style. I love the juxtaposition of a suit and a hair bow. That I’ve always done, but I think now I’ve really been playing between the two. I just bought a Simone Rocha blue dress that I’m going to wear this week.
Did you find any new challenges and differences leading Cosmoand Seventeen that weren’t present at Highsnobiety, and vice versa, aside from the fact that you’re in charge of multiple publications?
I love that the team is based in New York. Highsnobwas very global. It was a different skill managing across time zones. It’s exciting that we’re all in the office every day and we get to gather so often in real life. That’s special and amazing.
Fit Three
What advice could you offer a young writer or creative who might be interested in writing?
Just write what you want to write and don’t write what other people want you to write. Carve out your POV and your voice and define it. It’s easy to write what you think people want to read, but What do you actually want to write? is the real question.
Was there a seminal moment in which you first became interested in clothing and style?
My whole life I’ve been interested in fashion magazines. It was always a way that I expressed myself. It was writing and fashion. There was nothing else and it was almost like drinking water. It was how I communicated.
Even when you were a kid?
Yeah. I was a dancer, but it never made me feel quite like how fashion and writing made me feel. Collecting fashion magazines was so inspiring. It was like, Wow, my two interests combined.
Your parents weren’t interested in it?
I think my parents have cool style, but they didn’t care about it in the way that I do or did.
Fit Four
Are there any core tenets to your style?
Suiting, tailoring, platforms. Those are the main things.
What is it about suiting that does it for you?
Just feels nice. It makes me feel confident. It’s just how I feel the most comfortable, genuinely. I also think it’s a sign of respect to wear a suit and come to work every day. I really do respect my job and I respect where I work and what I do. There’s a certain amount of appreciation where it’s like, I dressed up for this thing that I do every day that I really like.
Can you remember your first significant clothing purchase?
When I wrote my first cover story, I bought a vintage Ralph Lauren suit. It’s funny, I was telling someone this weekend, I never really ended up wearing it because it didn’t fit me and I was like, Am I going to pay more to get it tailored?
What was your most recent purchase?
That Simone Rocha dress on eBay. I am getting it tailored and I’m so excited about it. It looks like a vintage prom dress, but I think after it’s tailored, it will look more like her most recent collection. It’s old. I think it’s from 2021, so it’s not recent, but it’s a perfect dress. I’m excited to wear it.
Fit Five
Are there some other brands that you’re loving at the moment?
Obsessed with Auralee. Kiko Kostadinov. Huge Kiko head. Chopova Lowena, I buy a lot from. Tory Burch. I love Bode. I have a red sweater that I was wearing today too. It’s dark red. I love, love, love Bode. It’s so well-made and it’s the quintessential “buy less, buy better.”
Does it bother you when people really hop onto a brand that you were on early before the hype?
No. I want Emily to blow up and as she has blown up; I’m happy for her. I’ve been obsessed with Edward Cuming since Brandon, our fashion director, told me.
If you had to wear one outfit for the rest of your life, what would it consist of?
A Thom Browne suit or Ralph Lauren vintage pants or Armani.
What about shoes?
My Prada loafers probably.
And then what underneath?
A shirt and tie. But never tucked in properly. And never on top of a T-shirt.
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