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

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.