Jason Bolden Shares His Journey to Becoming a Celebrity Stylist

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This month, Who What Wear is celebrating its 20th anniversary. To commemorate two decades of spotlighting tastemakers and style leaders, we’re dedicating October to guests who have shaped the fashion industry and cultural conversation since Who What Wear’s inception. This week, it’s Jason Bolden!

Bolden, one of Hollywood’s most influential stylists, got his start in the industry “accidentally” back in 2011 after his good friend Gabrielle Union asked for help finding a look for an event. On gaining momentum, Bolden says, “It took a while for a lot of people to recognize the body of work and the point of view.” However, his roster of clients soon grew.

Since launching his career as a celebrity stylist, Bolden has worked with the likes of Nicole Kidman, Cynthia Erivo, and Michael B. Jordan. For the latest episode of The Who What Wear Podcast, Bolden sits down with Hillary Kerr to discuss getting his first big break in the styling industry, how he grew his loyal client roster, and how he developed his distinctive styling philosophy.

To read excerpts from their conversation, scroll below.

Can you walk our audience back to how you got started in this wonderful, wild industry?

I come from this classic Midwest family setup, so I thought I only had the options of doctor, attorney, teacher. But I was really lucky to have a grandmother who was obsessed with fashion and who would allow me to experience Saks Fifth Avenue with her and Neiman Marcus and Christian Dior, and the names go on and on. I got to experience it through her in that way, but I never knew that this could be a job.

So I go to Chicago, and it was kind of like my fashion mecca. I would go into these thrift stores where they would have anything you can fit in the shopping bag for $25. Then eventually, I would take all this stuff … back to my apartment, and we came up with this idea of this modern approach to vintage.

We did a pop-up, and we had this store called the Garment Room in SoHo. It kind of made a life of its own, and we were selling everything and working with everyone from Akris to Ralph Lauren. We were doing these design-inspiration suites for them.

And then I just get a little burnt out. I take some time off, and as a good friend does, I get a phone call from a friend, which was Gabrielle Union, and she’s like, “I’m going to Art Basel. I need something to wear. Bring me some stuff.”

And I’m like, “Ah, fine. I’ll go there.” I bring her this vintage Lanvin dress, and she ended up wearing this multicolored polyester Lanvin dress from the ’70s.

I wasn’t trying to be a stylist. I was just literally helping a girlfriend, and then I get a phone call from a publication. It was like, “Hey, we want to talk about this look.” All of a sudden, I read it, and it was like, “purveyor of fashion Jason Bolden.” And I was like, “What? Like what? Now, I’m a stylist.”

How did you start to decide, How am I building my roster? How am I building my client list? Who should I say yes to?

It took a while for a lot of people to recognize the body of work and the point of view. It took a while, but … what ends up happening is you put your horse blinders on, and you stay focused on the path. I had those on, but I always wanted to collect people like I like to collect books. I wanted to create what I wanted the perfect dinner table to look like, and that’s what the clients began to look like—everyone from musicians to artists to directors to writers.

I want to talk about how you and Cynthia Erivo got together.

I get a phone call a night before [a shoot], and they say, “Hey, she’s shooting a cover of a magazine. Would you be able to shoot her for this?” I was like, “She’s already working with someone, and that’s just not my thing.” And they were like, “Well, the person isn’t available.” I was like, “Okay, this is the plan. I will come. I will set up. I will see her. I will show her the three looks, and then I’m gonna leave my assistant.”

I go in. I meet her. I show her these three looks. And we’re laughing, and she’s super funny. I put her in the Fendi, and I’m like, “Okay, this is it. I leave, right?” I get a phone call saying, “Hey, would you want to do the Harriet tour?” And then that was the beginning of a relationship.

I came in, and I told her how I saw it: “Let’s show the world what they’re missing because they don’t know quite yet.” Sometimes, you have to be a little bit loud, but not the type of loud where people want to turn the radio down—the type where you want to turn it up and dance and sing with it, right?

It’s one of those things where you get to work with one of those people who is a unicorn, and those don’t come across that often in this business, where you have style, personality, acting chops like no other, and then the humility of this amazing woman who just wants to serve and service the planet. That stuff is rare.

This interview has been edited and condensed for clarity.