In our long-running series, "How I'm Making It," we talk to people making a living in the fashion industry about how they broke in and found success.
When Jason Bolden answered my call from his office in Los Angeles, he was looking for his crystal to catch a moment of zen right before a potentially stressful fitting. Honestly, the rapidly rising (like, lightening-speed) celebrity stylist needs to take advantage of zen when he can, because his roster is packed — and growing exponentially by the day. Bolden's client list includes the most talented, inspiring and influential artists and entertainers making an impact on American culture and society today: "Selma" and "Wrinkle in Time" director Ava Duvernay; "Empire" matriarch Cookie Lyon, Taraji P. Henson; "Grown-ish" star and activist Yara Shahidi; and, most recently, Amy Sherald, Michelle Obama's official portrait artist.
The two were mutual admirers of each other's work via Instagram and the opportunity to dress Sherald for the historic unveiling of the 44th POTUS and FLOTUS portraits just "popped up." After emails, calls and a fitting at the iconic Hays-Adams hotel in Washington, D.C., Bolden dressed Sherald in a crop top and skirt outfit from the Dion Lee spring 2018 collection and pearl-accented lace pumps by Nicholas Kirkwood.
"To play a small part in such a historic moment is gratifying and humbling all at once," he says. "To underscore the whole moment: young black boys and girls will visit the National Portrait Gallery and see themselves represented — and that's powerful."
The self-described skater kid from St. Louis held an ambition to enter the fashion industry, and he, as many do, fell into styling. He moved to Chicago to study pre-med at Northwestern University, but then transferred to the Art Institute. After spending all his money upon arrival, he started working in luxury retail on the side. He started at Cynthia Rowley, moved up to Louis Vuitton and Gucci and amassed an impressive list of "uber-wealthy," but non-celebrity area clientele. (Although, he did have an accidental celeb gig, styling singer Martina McBride over the phone while at Nicole Miller.)
Bolden eventually moved to New York and opened The Garment Room, a vintage store in Soho on Greene Street, where houses like Calvin Klein, Akris and Ralph Lauren would come to source design inspiration. Entrenched in the fashion scene, he developed a close friendship with actress Gabrielle Union, who unintentionally tapped him for his first official celeb styling gig for a trip to Art Basel in 2011.
"She's like, 'Just find me something from your store to wear. Just bring it!,'" says Bolden. "It was a friend moment and I put her in this vintage Lanvin [for a Vogue party] and it just went crazy."
Opportunities "snowballed" from there, but after a year Bolden struggled to find his "point of view" and wondered if he should return to the corporate fashion world. But then he hit a lightbulb moment with good friend, neighbor and a pre-"Empire" Henson, during a shopping trip.
"She literally said to me, 'well, you need to get it together because I'm about to blow the fuck up and you're gonna be busy,' and literally from her mouth to god's ears: transition," he explains. "It was like boom, boom, boom, boom and everything back-to-back and I became this — it is what it is — go-to for all the amazing brown girls, which I die for. That was the start and, for the past three years, it keeps exploding even more."
Also on Bolden's client list: "Creed" and "Black Panther" director Ryan Coogler, actress and Louis Vuitton muse Sasha Lane ("the coolest girl"), Disney star Sabrina Carpenter and soon-to-be-breakout "Wrinkle in Time" star Storm Reid (more on her in a bit). Bolden doesn't just dress his clients. He creates these thoughtful fashion "moments," as he likes to say, to strategically build their aesthetic, parallel to — and possibly propelling — their career ascents, all while maintaining a specific point of view for each one. (Bolden also works on the other side of the red carpet, commentating for E!, and is a partner in a multi-disciplinary design studio, JSN Studio with his husband and interior designer Adair Curtis.)
Despite his awards and premiere season packed schedule, Bolden took time out to have an insightful, incredibly fun and refreshingly no-bullshit conversation with Fashionista about how he and Shahidi immediately clicked, what he has to say to those design house PRs who refused to dressed his clients early on and why it's an interesting time to be both a red carpet stylist and E! talking head in the age of #TimesUp. Here are the highlights.
Your clients all have their individual style and point of view. What is your styling philosophy?
What helps me bring out everybody's personal style and point of view is that I'm interested in interesting people. Smart girls. Powerful women. So that, in itself, leads me no other way but to be creative and help and enhance the look that's already there. What's kind of amazing is, I hear people say, 'oh, you can see that's Jason's girl,' but all my girls can be on a carpet together and it does. Not. Cross. It does not look like they're pulling from the same rack because they don't. Everyone has their own point of view because I style that way.
Like, Ava's into architectural strong modern things, but her personality pushes it even further than that. It goes super modern, super young, super fresh. It's completely different than a Taraji, who's my wild card. You just never know. Everybody has their own story, but in the big picture, it all makes sense. Because, honestly, I want each girl to have an amazing fashion profile, but at the same time, I want it to be very distinct and very theirs. It actually helps when the talent is smart, confident and strong. It makes my job so much easier.
How did you start working with Yara Shahidi?
Her publicist reached out to my agent, and this is also my manifestation: Yara was on my vision board and I had forgot because I had started a new one. I met her and our first experience [was her first appearance on 'Jimmy Kimmel Live' in May 2017]. It was a trial. They were testing out different people and I've never done a trial before. Normally it's very, 'I like you, I want to work with you.' Now I'm like, 'Game's on. I've gotta kill this.'
Some people come from this place where they're expecting this stylist to come with 95 pieces, but I'm not like that, so I always come in with like a garment bag. I literally presented her nothing but Marni because I had this idea in my head: I only want her to be in Marni. And we tried everything and literally we loved everything. So we were going to go with this beautiful printed Marni dress (and I put it on my Instagram a while ago as a throwback to our first fitting) and we loved it. The next day was the actual show, so I walk into the room — this is literally our first time working with each other — and Yara is sitting in the chair and I said, 'Yara, I had a dream, you cannot wear this dress.' She turned around and looked at me and says, 'I was thinking the same thing!' That was the beginning and what sealed the deal. It's been cookies and hamburgers since then.
With Shahidi, you've really taken her personal style, energy, intelligence and persona and translated that into her looks on the red carpet. What is it like collaborating with her?
I've been really lucky with my manifestations being I only want to work with people who trust me. Like some people come into fittings with 17 rolling racks and 9,087 options and 45 pairs of shoes. It's not like that. My girls trust me. I edit all the way down before I get to them. We're literally only looking at three looks.
For example, Yara wore custom Prada to the Emmy Awards. I said, 'Yara, this is the idea, I want you to have a Prada moment, like you'd get another step for your profile.' I showed her three ideas. Everybody thinks it's very super philosophical [to work with her], but if Yara cannot do the robot in her dress — or we're not laughing about it during the fitting, the chat or the sketches — it will not happen. We spend more time laughing and talking about things that are happening on the planet versus, 'Uh, this dress needs to be like this, this dress needs to be like that.' Because it's so edited by the time we get to them, our conversations are so short about it. The Emmy dress came, I brought it on set at 'Grown-ish,' she tried it on. It fit like perfection. She did it the robot and we wore it on the carpet the next day. That's literally how it happens with her.
When I say we spend more time talking about what's going on on the planet — we're very conscious of particular brands and where they stand. [We] find these independent, young, up-and-coming designers who stand for something and who actually can relate to Yara's fan base. So we do have those conversations and that does sway who we use and who we don't use, but minus that, it's pretty easy.
What is your approach in mixing both traditional, established designers with cool, young hip and under the radar ones for your clients?
I used to be the guy who read every fashion magazine on the planet and I don't really anymore, because I realized for me, the culture, the style, the It Factor is what we see around us. I'm a skateboarder kid at heart — that's what I come from. I just remember having really interesting stores growing up in St. Louis, like a privately owned boutique that has really cool interesting something and I would just buy it because it was great. I still have that kind of like same philosophy, if I see something really amazing and dope, I just like, 'We should try this.' My goals aren't really hung up on the brands of it all. I like the juxtaposition of it all. It's reality. I think it's wack — I don't think it's fashionable, I don't think it's chic to be always draped in, like, Vuitton. It's kind of corny. Those days are over. Luxury now is relaxed.
Did having all that luxury retail experience help you with establishing relationships with fashion houses when you started styling?
No. Not at all. There are a couple of really amazing PR people who actually get it and their style is on the pulse. [But otherwise, I was] presenting Yara, presenting Taraji, presenting all these different people at one point and people are like 'no, no no no.' But then the next month, something pops up amazing and all of a sudden they're like, 'we want to do it!' For us, that is not authentic or organic, so we have to pass on them. It's like if you didn't get it before, you definitely can't get it now. A lot of the brands you see me put on clients are because they have always got it from the beginning. I'm very clear on that. That's why when I look at my girls, it feels like they're supposed to be in these huge brands. There's people now that approach, all day long, 'We want this, we want this.' It doesn't make sense because you were never interested and now you're too late to the game, so it's not interesting. It's just kinda wack.
You're now in the position to help young, up-and-coming brands out, too. How do you discover them?
Instagram is completely amazing, and having a team that are a little bit younger than me and goes out more than I do. Also, when I go back home to St. Louis, I'm talking to my cousins who are like, 'Have you seen this, this person, this.' I'm still skateboard culture, so all my friends who are my age are skateboard people, like my friend Treis Hill who owns ALife, then my friend Brendon [Babenzien] who used to be the Creative Director of Supreme and now he owns the company Noah, we all still live and breathe that casual cool luxury life, so it's easy to find things like that.
I can already tell that Storm Reid will be making headlines for her upcoming 'Wrinkle in Time' promo tour. What's your approach when it comes to styling her? What should we expect?
Expect young fashion. Storm is almost six feet tall in heels. She's like a model, but she is a genius actress, so clothes love her. She has the best personality. She's from Atlanta. She's warm. She's bubbly and she's exactly what 'Wrinkle in Time' is. What we're going to do for the first premiere is going to be really, really amazing. I think what happens a lot of time, you get these young actresses and people kind of push them, like they instantly become these fashion icons and then you give them nothing to grow to. The idea, just like with Yara, the idea is it's a slow and steady race and it's like each part of your career means something else.
Her large introduction is standing next to Oprah, Reese [Witherspoon], Mindy [Kaling], Chris Pine and director Ava Duvernay. That's a whole crazy platform. So the style and the way we're going is young and it's still fashion and the brands we're going to be using are very conscious of those, but still making them relatable. That's the thing: She's 14. She needs to be relatable. It just makes a lot more sense to us because I come to it from a brother/uncle side to it. People fall in love when a girl seems very endearing and lovely and warm, versus someone coming out being overly fierce. You're like, 'whoa, whoa, whoa, you're 14. It's weird.' There are a lot of brands now that are really interested, but it's a bit mature and it just doesn't make sense. When she's 17, 18 that will be the perfect brand.
What do you have coming up for the Oscars?
Allegedly I have three [clients] and I'm really, really excited about this one, if everything plays out. I did the fitting and I had to run out because I had to go meet another client. I literally ran to the elevator, pressed the button, ran back into the studio, I was like, 'Ahhh! This shit is going to be the fucking Gwyneth Paltrow pink Ralph Lauren Oscar moment!' Everybody was like, 'Huh? You're insane,' and then I stormed out.
You're doing the E! red carpet commentary and it's such an interesting time to be covering the carpet and working from the stylist side during #TimesUp when everyone trying to figure out how to acknowledge fashion. What's your perspective on that?
I think Times Up is exactly what it is: Time. Is. Up. And we should spearhead that. We should circle all this back around to the whole bottom line about equality. Let's fight for equality, bottom line: black, white, gay, transgender, Asian, all of it. It needs to be one huge conversation. Everybody wants to be treated as an equal. So that's what I have to say about that as a whole.
Experiencing it for E! for the Golden Globes, it was the first time that that whole thing happened on my side as a stylist. It was crazy-town, like trying to get a dress. Because all this stuff is pre-planned and then when the blackout decision was made, a lot of stylists were in a frenzy. Because you may have had this Sonia Rykiel pink gown made, and now you have to switch it, which becomes another problem because then you have brands also committed to someone or you don't have time to get a black dress or one stylist might be hoarding every black dress so the planet. I had two girls that were supposed to go, but then Ava only went. I was lucky enough that Armani Privé did a custom gown for Ava and it was spectacular.
But then the climate on carpet was very uncomfortable. You could see that in some of the energy. They didn't know what to say, because, again, it was the first time, you also didn't want to say the wrong thing. I think going forward it's going to be a little bit easier to have these conversations and still maybe ask someone what movie they have coming out and also what they're wearing. So I feel like once we get into the groove of it. I think it should work itself out and hopefully the all of it, the whole bottom line of equality, hopefully that works itself out, too. Period that.
This interview has been edited and condensed for clarity.