Willa Bennett is Caught Red-Handed

Caught Red-Handed is a monthly interview series that begs the questions: What do cool people actually consume? What are their digital vices and indulgences?

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Our guest this month is one of the media world’s brightest stars. Willa Bennett is the editor-in-chief of Highsnobiety, a digital editorial that spotlights everything from the sneakers you wish you could wear but don’t have the swag to pull off to the emerging indie artists you’re grateful to read about so you can trick your next Hinge date into thinking you have good taste in music.

Essentially, Willa curates cool for a living.

Her Instagram hosts an enviable mix of famous faces, FOMO-inducing after parties, and impeccable fashion. So I was dying to know – can anyone really be that effortlessly cool 100% of the time? What batshit videos is this person watching on TikTok at 4AM? Is she queuing up Dirty Dancing on a night in, or staying faithful to the Criterion Collection?

Luckily for me, Willa was gracious enough with her packed schedule (ever heard of Cannes, anyone?) to give us the down-low.

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Emma: You became editor-in-chief of Highsnobiety at age 27, a stat that makes me question my life and want to vomit simultaneously. When you’re dealing with the stress of Executive Level Business, what’s on your playlist to pump you up and get you in the right headspace?

Willa: I listen to music the most when I’m walking home from work. The Highsnobiety office is within walking distance of my apartment, and I have to make many important decisions quickly, so the calmness at the end of the day is relaxing for me. I love phone calls by the water — with my best friend from high school or my partner — and when they’re too busy to talk to me, I resort to a playlist that ranges from Central Cee to Montell Fish (two young people I’m proud to say have been in Highsnobiety).

Emma: You recently moved to the West Village, so let’s talk about some of the most cursed brunch spots there. F, Marry, Kill: Jack’s Wife Freda, Sadelle’s, Butcher’s Daughter.

Willa: This is an awful question. I’d marry Sadelle’s and kill the rest. My favorite West Village spots are Via Carota, i’Sodi, and Commerce Inn (all queer owned too). Minetta Tavern and Bar Pitti are classics too. I find these places (and the West Village) so romantic.

Emma: Part of your personal brand has been built around your menswear expertise, and last year you told Vogue that you own more than 100 ties. I’m sure the vast majority of them are very chic, but do you have a favorite novelty tie you can share with us?

Willa: I have a few vintage Ralph Lauren ties from adolescence that are very special to me. Ralph actually gifted me a black embroidered tie when I started at Highsnobiety, and it’s a recent favorite.

Emma: Having spent much of your career working in social for some of the world’s biggest media brands, I’d love a peek into what your TikTok algorithm looks like.

Willa: My FYP is the perfect mix of fashiontok (some of my favs at @thatadult and @needforbreed) and queer creators (@hina & @gracevalentine). It’s a pretty predictable answer coming from me — but it’s true!

Emma: What’s your favorite guilty pleasure movie?

Willa: I recently re-watched Desert Hearts and found it so beautiful. The suiting, queer love, all of it — still thinking about it weeks later.

Emma: If you were forced to go on a reality show or never eat your beloved overnight oats again, which show would you pick?

Willa: Love Island, obviously.