How Top Stylist Jason Bolden Made 8 Stars Look “Expensive” on Oscars Night

Jun 15, 2023

By Christian Allaire

When awards season rolls around, top stylists are not only tasked with dressing some of Hollywood’s biggest celebrities for the red carpet, they also have to juggle multiple stars on the same day. That’s precisely what Jason Bolden did at this year’s 95th annual Academy Awards. The leading stylist dressed Michael B. Jordan, Vanessa Hudgens, and Jay Ellis for the official ceremony, and Jordan, Hudgens, Yara Shahidi, Dwyane Wade, Sabrina Carpenter, DeWanda Wise, and Trevor Noah for the after parties. It sounds like a Herculean feat, but Bolden is a seasoned professional. “You never know what’s going to happen that day: A dress can pop, or someone can fall ill,” says Bolden. “You have to be ready for the unexpected.”

Despite the extensive planning required to juggle multiple clients at the same time, Bolden’s Oscar preparations this year didn’t happen terribly far in advance. He says he began thinking about looks for his clients around the start of fashion month in early February. “Fashion [month] falls in between awards season, so you get to digest those new visuals,” says Bolden. From there, he began filtering certain collections to his clients. “I always take it back to the individual: I found out what collections or designers really speak to them and their point-of-view,” says Bolden. Often, this was done over text. “I’d get a text from Vanessa [Hudgens] being like, ‘What are we giving the kids?’ And then we’ll juggle a couple of ideas.”

Then time for fittings, which typically happen a week or two out from the grand event. Bolden says he favors an extremely tight edit when it comes to look options—an uncommon approach. “If we’re doing the Oscars, there’s probably going to be three options,” says Bolden. “And that’s a lot. If I bring more options to a fitting, my clients are like, ‘Is everything okay?’” This allows the fittings to be less about sifting through garments, and more about perfecting the winning look. “My fittings are about laughing, adjusting, and trying to make it fit perfectly,” says Bolden. “A lot of the time, I do one serious fitting, and then we try it on right before the person goes into glam. Then the tailor on-site makes any last minute adjustments and tweaks.” Something else that’s surprising about Bolden’s process? He waits until the day-of to source and pick the jewelry. “I’ll have an idea of it,” he says.

This year, those fittings resulted in a wide range of styles. For the main ceremony, Bolden dressed Hudgens in a vintage strapless Chanel dress; He also put Jordan in a sleek Louis Vuitton suit with two ornate brooches. “We wanted to go super dapper, super smart—easy Hollywood,” says Bolden of the latter look. “Nothing pretentious about it.” For the after-party ensembles, he embraced the experimental. He dressed Yara Shahidi in a red leather dress adorned with floral appliqué from Bottega Veneta (with matching gloves), and Carpenter in a sheer Paco Rabanne gown with embellishments covering the bust. “The after-party looks are when you can take it to the max, and be a little more playful and wild,” says Bolden.

While he played around with many different aesthetics this year, Bolden says there was a through-line present throughout his work. He wanted his clients to embody one word: “expensive.” His ensembles embodied a sense of luxury—but easy luxury. “My grandmother used to always say to me, ‘Real luxury is leisure,’” he says. “I wanted the looks to feel so easy and so comfortable that it feels like leisure.” It’s a spirit Bolden even channeled with his very own look on Oscars day. “I’m strictly uniform,” he says. “I’m always in a pair of black Chrome Hearts sweatpants and the matching hoodie. With a pair of Birkenstocks or super old Vans.”

Once he sent his flurry of stars out on the carpets on Sunday night, Bolden says he celebrated by watching the event on TV with some fellow stylists. Now that the Oscars are behind him, however, the stylist won’t be resting—he’s going to be dressing Shahidi for her upcoming Peter Pan & Wendy press tour in April, for one. Still, he will be rewarding himself for all of his hard work this awards season. “I always buy jewelry,” says Bolden of his post-Oscars tradition. He already has his eyes on something fabulous. “There’s this vintage Van Cleef flower ring, it’s made of sapphire and white diamonds. It’s incredible. It’s going to look so good with my sweats on.”

Below, an inside look into Bolden’s Oscars day.

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