Jessica Willis has been the fashion director at The Cut, a hugely successful digital offshoot of New York Magazine since 2021; a bi-annual solo fashion edition in print launched in 2024. Willis, who recently styled and designed the costumes for Samuel L. Jackson, Serena Williams and Kendrick Lamar’s dancers for the Super Bowl LIX Halftime Show, has styled the likes of Julianne Moore, Kacey Musgraves and Naomi Campbell for The Cut. She has also worked on editorials for W Magazine, WSJ, Vogue and campaigns for Apple, Calvin Klein and Jil Sander alongside projects such as, Solange’s album ‘When I Get Home’ and Kendrick Lamar’s music videos ‘Not like Us’ and ‘Squabble Up’. She cut her teeth working at a costume house in Los Angeles, before touring with the Black Eyed Peas and styling her own music videos for artists including Azealia Banks. She made her initial transition into fashion with a post at Urban Outfitters in Philadelphia before working across both fashion advertising and editorial.

1. Tell us about an early clothing of fashion memory?

It was the collection that Chanel put out when Karl [Lagerfeld] was inspired by Lindsay Lohan and her [prison] ankle bracelet [spring-summer 2008]. I bought those Chanel booties with the little pouch on the side. I was working in retail and it was my first big purchase. My mom was like ‘What on earth?’ [laughs]. I told her they were an investment! I was in my early 20s. I just really appreciated the cultural referencing and the wit. I was living in L.A at the time too, so Lindsay Lohan, Paris Hilton, Britney Spears, all of that paparazzi noise was so much a part of my culture.  

2. You have styled some of the music industry’s finest. What have you most learned from these collaborations? And what music is bringing meaning to you at the moment? 

Working in music, everything is fast and everything changes a lot. It taught me to problem solve. I think that is a really important skill to be able to pivot and not sit in the problem. I'm just a curious person by nature. I like to learn. So if I'm not learning, I'm kind of bored. Everything for me started when I saw the William Klein movie ‘Who Are You Polly Maggoo?’ The opening scene has all these wearable sculptures in it, so I just made my own take on those, which ended up in an art show and that’s how I met one of the costumers in L.A who was working on stuff for Katy Perry and then Lady Gaga. It all came through curiosity and feeding my creative need and by being open to new experiences. 

How did I feel at the Super Bowl? I felt prepared. My whole journey had led me to that. It was like going back to where I started. 

I’m listening to a lot Cleo Sol at the moment. I think it’s just the time that we’re in. I like her positivity. Her music is like positive affirmations, and I think that is really important. There’s a lot going on right now.

3. How would you define beauty?

I think it's just confidence. I always think about Rihanna. Rihanna is the ultimate, she could do anything. She’s just confident in her skin and that is really beautiful. She’ll take a beautiful photo, and she’ll take a photo that isn’t technically deemed beautiful. She did a shoot with Nadia Lee Cohen and was able to take it there, and play a character. That’s so beautiful, just being open.

4. It’s fashion month. What ingredients are you looking for in a great runway show? 

When I see brands that have storytelling and intention. I haven't seen a lot of shows yet [Willis is about to go to Milan from London] but I really love Simone Rocha. She has a signature that is just hers - she has a cult following like Rick Owens does - and I love seeing the evolution. It’s becoming sexier, she’s doing menswear, but it’s still very her. I also went to visit Michael [Stewart] of Standing Ground and I’m obsessed. He is someone that is so passionate and dialled in to his craft. We’re kind of seeing a lot of the same things over and over at the moment so when something stands out and is going against the grain, like Standing Ground, that’s really exciting. 

5. What one thing would you like more of? What one thing would you like less of?

I would say more, 100% more time with the people that I really love, and my friends that uplift me, make me feel good and who I can laugh with. On the other side, I’d just like less negativity. I don't know if that's real answer, but that's kind of something that I'm always trying to rise above, negative thoughts.