How Top Stylist Jason Bolden Made 8 Stars Look 'Expensive' on Oscar Night

When awards season rolls around, not only do top stylists have to create red carpet looks for some of Hollywood’s biggest names, they also have to juggle multiple stars on the same day. That’s exactly what Jason Bolden did at this year’s 95 annual Academy Awards. Head stylist dresses Michael B. Jordan, Vanessa Hudgens, and Jay Ellis for formal ceremonies, and evening for Jordan, Hudgens, Yara Shahidi, Dwyane Wade, Sabrina Carpenter, DeWanda Wise, and Trevor Noah. It might sound like a daunting feat, but Bolden is a seasoned professional. “You never know what’s going to happen that day: a dress will be in fashion, or someone will get sick,” Bolden said. “You have to be prepared for the unexpected.”

Despite the extensive planning required to juggle multiple clients at once, Bolden’s Oscars preparations this year haven’t been much ahead of schedule. He said he started thinking about styling clients when fashion month kicked off in early February. “Fashion [month] is right in between awards season, so you can digest those new visuals,” says Bolden. From there, he started filtering certain collections to his clients. “I always feed it back to the individual: I find out which collections or designers really spoke to them and their perspective,” says Bolden. Typically, this is done through text. “I’d get texts from Vanessa [Hudgens] that would be like, ‘What are we giving the kids?’ And then we’d think about some ideas.”

T Fitting time, usually within a week or two after the grand event. Bolden says he likes extremely tight edits when it comes to appearance options—an approach that’s not often seen. “If we had the Oscars, there could be three options,” Bolden said. “And a lot. If I bring more options to fittings, my clients say, ‘Is everything okay?'” This makes fittings less about screening garments and more about perfecting a winning look. “My fitting is about laughing, adjusting, and trying to get it to fit perfectly,” says Bolden. “A lot of times, I’ll do a serious fitting, and we’ll try it on before the other side starts to flamboyant. Then the tailors on set will make last-minute adjustments and fine-tune.” Are there any other surprises about Bolden’s process? He waited until the day of sourcing and selecting jewelry. “I’ll have an idea,” he said.

This year, these accessories resulted in a wide range of style. For the main ceremony, Bolden dressed Hudgens in a vintage strapless Chanel dress; he also dressed Jordan in a stylish Louis Vuitton suit, complete with two ornate brooches. “We wanted to be super sophisticated, super smart—simple Hollywood,” Bolden said of the latter look. “There’s nothing pretentious about it.” For after-party ensembles, he’s open to experimentation. He donned a red leather skirt with Bottega Veneta floral appliqués (with matching gloves) for Yara Shahidi and a sheer Paco Rabanne gown with embellished bodice for Carpenter. Says Bolden: “After-party looks are when you can go the extra mile and get more playful and wild.”