Coolest Person in the Room: Dylan Kelly

How was your Fashion Week? Before we get into it.

It was fun to see everyone. I always feel like it’s a homecoming in a way. You haven’t seen everyone all summer, and then you’re at the shows. And it’s cute to bump into people and catch up. That was the fun part.

Congrats on leaving your full-time gig to pursue your own thing!

Thank you. I’m honestly really excited for this new era, and definitely nervous, because leaving a publication and going creator is just an interesting pivot. But I’m excited. I think it’s what I wanted.

What did your journey look like becoming a writer and editor?

I want to give PAPER a proper shout-out, because it really all started there. I was an intern, so it feels so full circle to be featured in this story. I honestly can’t believe it. PAPER embodied that magic about fashion that made me so excited to be involved.

I was going to Tufts, and I really found myself through fashion there. I saw it as a vehicle for self-expression, and coming out as a gay man, I needed that. In San Francisco, where I’m from, it was more difficult to go against the grain, especially in high school when you just want to fit in. But in college I used fashion to discover myself. When I was in Medford, Massachusetts, I wanted to get into fashion, but it was very difficult. I ended up transferring to FIT, and once I got there, I hit the ground running with editorial internships. I always wanted to write, so it felt like the right segue into the industry. I started at L’Officiel, then went to V Magazine for a year and then landed at PAPER. That was my last internship before graduating from FIT.

I started at Hypebeast a month or two later and was there for four and a half years. My role switched so much. I was hired as a writer, basically to pump out five news posts a day, one or two features per week, and just keep the news cycle going. At first, it wasn’t even specifically fashion — I was doing tech and everything. But over time, I carved out a space where I was doing fashion news coverage, features and then ultimately social media coverage. That blossomed into video scripts.

Is that what inspired the pivot to making your own videos and becoming a creator?

By the end, there were no KPIs like before. It was more important in some cases to do a video than an article. As the industry shifted from writing to short-form video, I wanted to see what I could do in that space myself. The videos I started making didn’t necessarily align with Hypebeast’s voice, so it made sense to try them on my personal page. The team at Hypebeast even joked like, “This is totally unique to you. We would never run this here, but we’re so glad you’re trying it on your page and it’s working.”

I posted the first one on July 7th, and it’s been just over two months now. It’s completely changed the trajectory of everything I’m doing. I feel like the momentum was there, and I needed to take the leap to focus wholeheartedly on it. It’s been insane and so exciting.

I feel like with Instagram, they always say people do well with a series.

Yeah, they always push a series, and they say consistency is key. But it’s different for everyone, whether it’s the quality level of your videos or the bandwidth you have to post often. Still, a series is what really hooks people.

What do you think it is about your “Walk With Me” series that is resonating with people?

I was shocked, honestly. The first one I posted is still the most viewed. It was about the Dior tie on one of the collars that Jonathan Anderson did at Dior, and then A$AP Rocky wore it at the show. That tie was inspired by Basquiat. A$AP Rocky ended up seeing the video and commenting, which shook me to my core.

What resonates with people now is that I introduced a character they’re slightly familiar with. Obviously, it takes cues from Miranda Priestly’s cerulean monologue in The Devil Wears Prada. But on the internet today, introducing a character that’s personality-driven locks people in longer. Being in character also helps me articulate the fantasy of fashion — why designers are inspired and the manifestos behind collections. Acting it out has been fun. I tell my friends I accidentally launched an acting career, because I’m out in the streets embodying this character. Who you’re talking to right now is not who you see in those videos; it’s an alter ego.

It makes fashion more fun while still being political, divisive, and necessary. I can bring those sides out through the character too. It’s not just frivolous; it’s layered.

I love the idea of making a character. Everyone else is chasing authenticity, but you’re showing you don’t have to.

Exactly. It actually makes me feel more at ease, because so many new eyeballs are on what I’m making, but it’s cute since it’s a thing I created.

These videos feel more aligned with me than the ones I made for publications, which had stricter codes. I’m a fun person — I was in musicals in high school — so the theatrical element excites me. The authenticity is in the excitement you see in me making the video. But everything else? That’s an act.

Of course, this is all new and you just left Hypebeast, but where do you see it going, and where do you want it to go?

It’s fun to think about new ways to tell fashion stories. I see these videos as a different version of an article, written in this voice and performed by me. I want to create different verticals with this character in new dynamics.

I love “Walk With Me,” but I want to expand, create different atmospheres, have my character talk to people, and maybe even write to people. I want to expand the universe around this persona. There’s no strict North Star, unless it’s [becoming] Miranda Priestly.

It’s good to have a broad goal and just take opportunities as they come.

For sure.

Well, thank you for talking to me!

It feels crazy that I’m even doing this interview. It’s so wild that I’m speaking to PAPER as the interviewee.

Photography: Diego Villagra Motta
Styling: Angelina Cantú
Lighting design: Peter Demas

Styling assistants: Quinn Tommy Herbert, Olu Adeleke

Executive creative producer: Angelina Cantú
Fashion editor: Andrew Nguyen
Story: Andrew Nguyen
CCO & CEO: Brian Calle
Location: Pearl Box