FIRST DIMERS: Willa Bennett

Interview by Brynn Wallner, photos by Cobey Arner 
March 2022 
          Willa Bennett and I met on the internet, which feels appropriate as both of us have careers (and lives) inextricably linked to it. Rather than dismissing the internet – or social media, specifically – as a brain melting waste of time (my words), Bennett understood its power of connectivity early on. She’s currently operating as the Associate Director of social media at GQ, a role she landed after successfully building out social programs at various outlets since graduating college (securing her a place on this year’s Forbes 30 Under 30 list, thank you very much). When you passively scroll through Instagram, you’re inadvertently being impacted by her pioneering work of shifting and developing the way media brands communicate with you, their audience. It’s Willa’s world, and we’re just living in it! Or rather, she’s steadfastly dedicated to creating a world more representative and nurturing for the next generation to live in.

For someone so online, it’s refreshing to hear how “real life” and tangible objects play into her sense of self. Her ties, for example, are a personal style signature that carry far more meaning than you could imagine. And then there’s her vintage Rolex Bubbleback, an incredible piece she inherited from her father with an incredible story to match. Don’t you wanna read about it now???

Brynn Wallner: First, tell me about the ties.

Willa Bennett: I was a very serious ballet dancer growing up, but I always struggled with the uniform I had to wear to dance class – you know, black leotards, light pink tights, ballet shoes– it all felt too feminine for me. I started adding items that felt more me, like a huge oversized blazer or a vintage tie. I wrote about this in GQ last year, but falling in love with menswear also coincided with me coming out as queer. I really value personal style and do feel most myself in ties. 

BW: It’s such a signature. So, when did you move to New York?

WB: I moved to New York when I enrolled at Sarah Lawrence in 2012. I still studied dance pretty seriously throughout college, but I always wanted to be a writer. I took almost every writing class Sarah Lawrence offered: poetry, profile writing, digital journalism, the art of the memoir. My professors would send me to the city on assignment to “talk to this artist for 20 minutes and write 10,000 words about them.” I loved those assignments because I love writing profiles (and talking to strangers), but I didn’t see this type of profile online anywhere. So, as graduation approached, I went to my advisor, and – I remember this day so clearly, I was in her office wearing a light blue tie – and I was like, I know what I want to do for my thesis. I want to go to a middle school for a month and observe how young people are absorbing digital media. I want to see what magazines they’re actually reading (IF they’re even reading them). She greenlit it on the spot and then I spent a month of my senior year at a middle school. My thesis only ended up cementing my belief that social media is the future of storytelling. I also wrote about how a lot of times, something will happen in a young person’s life, and they’ll go to their phone – specifically to Snapchat, YouTube or (which is now TikTok) – before they even told their friends or their parents. The internet is such a powerful tool. This led me to my first job out of college at Seventeen Magazine. I loved working at Seventeen because I felt like I was making a tangible difference in the lives of young people. I ended up running their Instagram (among other platforms) and I launched the brand’s first-ever identity vertical that’s still around today.

BW: Where did you go from there?

WB: I went to Bustle Digital Group, where I worked across audience development and, towards the end of my time there, helped with the relaunch of NYLON, a publication I read as a teen. Throughout it all, though, I feel like I've still been on the same pursuit: to make digital media more diverse and better for the next generation.

BW: I’m dying to read your thesis.

WB: It’s wild how outdated it already is. The social media landscape changes so quickly.

BW: You were very ahead of the curve!

WB: When I started in social, there weren’t social media professionals on magazine mastheads yet. Even at Seventeen, print and digital were actually on different floors in the Hearst Tower and rarely spoke to each other. In retrospect, that’s probably what excited me about it. Coming out of college with this research, I saw such an opportunity in this space. I’m really proud of the ways in which I’ve led the social team at GQ. I’ve hired a team of professionals and empowered them to not only meet the timely demands of social media but also program our platforms in a way that is forward-thinking and responsive to the zeitgeist. It’s been so rewarding, personally and professionally.

BW: Do you love working at GQ?

WB: GQ is made up of some of the most stylish creatives on the planet. We all have such specific taste and bring something different to the pages. I definitely see the world differently than many of my colleagues, but that’s why it works. I give our Global Editorial Director, Will Welch, all the credit for creating such a collaborative workplace. He is the reason the magazine is as cool as it is.

BW: Do you get to see a lot of watches at GQ?

WB: Yes, working at GQ has only cemented my love for watches. We have an amazing print column in the magazine that I genuinely look forward to reading each month.

BW: Okay, now tell me the story behind your watch.

WB: It’s my dad’s! He’s always been my style North Star. He bought it for himself when he lived in New York. The engraving was a surprise gift from my mother, years ago, when they were married (they’ve been divorced for decades). I’m still personally undecided about the engraving. Why would you surprise engrave anything on a vintage Rolex? I’ve come around to it though, especially because it’s my dad’s initials. I wear it every single day. I forgot to wear it one day this week to work this week, and I felt like I was missing a part of myself.

BW: I love the engraving for that sentimental reason. It’s also very bold to have the engraving on the buckle instead of the caseback. When you wear it, people can see it. So, you have sisters?

WB: Yes, I have 3 sisters.

BW: Are you the oldest?

WB: I’m the second oldest. There’s also Alfie, Finley and Scout.

BW: You’re named after Willa Cather?

WB: It’s almost like my parents knew I was going to be a writer. My mother was reading My Antonia when she was pregnant with me.

BW: Four girls, wow. Most people I talk with get into watches via their dad, but a lot of these people are guys. A father will pass their watch along to their son – you see this messaging in watch ads all the time. But I love when a dad passes it along to his daughter.

WB: It’s wild that we have the same initials, which I always forget because he goes more by “Bill” than “William.” This watch is a reminder of that, along with a Ralph Lauren button down embroidered with “WHB” that he also gave to me.


WB: Yes, we share the middle initial, too! My middle name is Haley, and his is Herschel.

BW: Did he plan it that way?

WB: He says he “doesn’t have favorite daughters” but… I would like to challenge that.

BW: I don’t believe that! It feels like you were selected. Alright, give me all the deets on the watch please. 

WB: Okay, here’s what my dad says [via text]: Your Bubbleback was bought at Aaron Faber in the late ‘80s – probably ‘89 on a trip to NYC. I think I paid $250 for it. Sometime in the early ‘90s (I suspect it was 1990, right before my 40th birthday) your mother, who had a fondness for monograms, snuck into a jewelry shop and had it engraved. I always thought that, since we shared the same initials, it would be an eventual gift to you. A few years ago, I took it to a great shop in Toluca Lake for an estimate, to clean it and find potential problems, etc. Mike, the owner, offered to find the rare Rolex pieces I needed to maintain its authenticity. He would have to go on eBay and watch forums to find specific parts original to the watch, if necessary, with one caveat: this could take months, and he could not estimate the costs. We agreed on this, and I would take the watch home until he found the two pieces needed. A few months later, Mike called to say he had received the parts and was shocked to find them reasonably priced. We had it cleaned and put in perfectly running order to wear once you were interested in owning it. My rough memory is that the serial number indicated the watch was manufactured in the late ‘40s.

BW: Wow, that’s all the information I could have wished for and more. The watch heads are going to love this. You wear it every day?

WB: When I wake up in the morning, it’s the first thing I put on. I check it before I check my phone, which is a big deal considering I literally work in digital media.

BW: I love that it’s so ingrained in your life. You wear it quite loose. Is that how it was sized for your dad? You didn’t get any links removed?

WB: I like it loose. I like it with my ties.

BW: It fits your spirit. It’s not super tight.

WB: There’s this photo of Zoe Kravitz wearing a loose watch, which is part of my inspiration.

BW: When exactly did you get it?

WB: It had its own debut in GQ! I first wore it to our “Man of the Year” party in Los Angeles, in November.

BW: Stepping out! Did you feel growing pains wearing the watch, or did it immediately complete your look?

WB: It immediately felt a part of me. When I write now, I need to wear my watch, and without it, I miss it. I also just love that I can look at the time on my wrist versus my phone because I look at my phone so much for work. 

BW: Is it your first and only watch?

WB: My first and only nice watch. I’ve had others.

BW: Like what?

WB: I had a hot pink Baby G in high school. And a Casio, a sleek gold one. The black classic Casios were the cool Queer Thing to wear at Sarah Lawrence, but I had a loose gold one without a buckle. I wore it on my right wrist, my ballet teacher hated it.

BW: Do you have any other watches on your radar that you’d like to add to your collection?

WB: I would love to collect vintage watches alongside my ties one day. Most of my ties are vintage and you can’t find them anywhere, and I’d love to do that with watches. Our mutual friend Jon Tietz and I send each other watches, ties, and suits constantly, and recently we’ve been fixated on loose men’s watches. I’d love to harness a collection that I can pass down to my younger sisters. Style is personal and I hope that as I get older I only continue to hone what I put on my body.