Meet the Stylist Behind Cynthia Erivo’s Flawless Red Carpet Looks

Jason Bolden talks about dressing this award season’s best-dressed star

Every awards season, one nominated actress seems to outdo the rest of her red-carpet competition. This year that honor goes to Cynthia Erivo, who’s up for Best Lead Actress for her portrayal of Harriet Tubman in Harriet, and is also known for roles in Widows, Bad Times at the El Royale, and as a supernatural savant in the current HBO series The Outsider. Next, she’ll star—and sing her heart out—as Aretha Franklin in the next installment of the PBS series Genius alongside David Cross and Courtney B. Vance.

After several months of walking red carpets around the world, Erivo’s emerged not just as acting and singing star—she’ll perform “Stand Up,” the Oscar-nominated song from Harriet during the ceremony on Sunday—but fashion star as well. That means the man behind the looks—stylist Jason Bolden—is becoming a bigger star in the fashion world than he already was.

Best known for dressing Taraji P. Henson over the years, Bolden also tends to the red carpet looks of Storm Reid, Yara Shahidi, Alicia Keyes, Janet Mock, Vanessa Hudgens, and supermodel Jourdan Dunn. He’s also created his own eyewear collection.

We asked Bolden about dressing this season’s best-dressed star.

How did you meet Cynthia?

I met her shooting the cover of Variety. We’ve been together for maybe four months. I got that cover by accident, last minute. I put her in a denim gown with white feathers by Balmain. I think that’s one of the first times Balmain was on the cover of Variety! That was our introduction. We laughed, our rapport was easy and causal. Instantly, I knew Cynthia was a fashion girl, the way she went through the racks. I got a phone call after asking if I’d be able to get 35 looks by Monday in New York. Ever since then, she’s been the talk of the red carpet.

Is Cynthia a fashion person in real life?

What you see on the red carpet is what she is in everyday life. Cynthia walks into fittings wearing [English avant garde designer] Simona Rocha. We had to do a fitting for The Today Show and she showed up in bright red patent leather Prada combat boots. She is what the fashion world needs at this moment! She likes to wear the hardest thing out of any collection. She’s fearless! The Marc Jacobs all-feathered pink dress she wore for the November premiere of Harriet, that was beautiful for the runway, but can it function in real life? She has this innate thing, she puts clothes on and looks six feet tall. She’s maybe really five-foot-two. She carries clothes like it’s no tomorrow. Both the Valentino couture gowns she’s worn—the kelly green silk to the Governor’s Awards and the Grammys huge Valentino Couture pink flora—both had so much fabric. Tiers and tiers. She just owns it. It looks like the clothes enjoy being on her.

How do you chose your clients—and the designers you pull from?

It’s very simple: I only work with people who get it! I’m very consistent. There are certain brands I don’t use. I think some brands are really transparent when it comes to dressing a certain color of skin, they don’t see any value in it. I love Valentino, Prada, Gucci, Versace, Tom Ford, Rosie Assouline, Etro, Schiapparelli by Daniel Roseberry, Alberta Ferretti. And a young designer named Charles Harbison, who’s dressed Beyonce.

How did you get started as a stylist?

By accident. I owned a vintage store in New York called the Garment Room in SoHo. One day Gabrielle Union called and said,” I’m going to Art Basel, come down to Miami and help me.” I put her in a 1970s vintage Lanvin polyester. Vogue picked it up and I became a stylist. That was about 12 years ago. I moved to L.A. five years ago. Initially I did all celebrity and VIP red carpet. I had lots of private clients. Then Taraji, then Monica and Brandy. I came here because my husband got a job here—I was kicking and screaming. Now I can’t imagine not living in L.A.

Once Cynthia got the Oscar nomination, did all the luxury brands come calling?

Designers are going nuts over her. If you’re a true creative and you see someone like her, you zone in on these people who will give life to your art. I met Daniel Roseberry from Schiaparelli at the Chateau Marmont a few months ago. That’s how that SAG gorgeous fuchsia tiered ruffled gown happened. He built me a custom gown in the middle of his couture show! Cynthia hadn’t even seen this dress. She totally trusts me. She never sees half the things I commission for her! We do 15-minute fittings with 12 looks—lightning rounds! I edit, edit, edit before the fittings so that I’m totally prepped. Sometimes we don’t even try shoes on—she will literally wear the same shoe from the Jimmy Choo to the Louboutin to the Stuart Weitzman. It’s all about the dress! The black-and-white sequin Thom Browne gown for the Globes (which took 800 hours and 11 people to make), the giant mosaic gown by Fendi Couture for the SAGS—it’s always the standout dress from any collection.

How did you decide on what will be her Oscar red carpet gown for this weekend?

When the nominations hit, Cynthia was on a plane to Japan; she found out on the plane. She couldn’t talk to anybody! In a moment, I found the dress, and I texted her to say, “GOT THE DRESS, THIS IS IT!” I kept sending her images, but it wouldn’t load. She finally got it. I said, “It’s amazing, isn’t it?” Her response was “Oh, yeah.” I called her and said, “Can you see this?” Turns out it was blurry. Then I showed her again and she freaked out.

“For me, being a black person, dressing the only nominee of color, it’s very impactful.”

She’s also performing at the Oscars. So she’ll need another dress, no?

Yes, two looks—it’s gonna be a really iconic moment. Culturally too. For me, being a black person, dressing the only nominee of color, it’s very impactful. This carpet we really want to show up in a way that’s larger than us. We might do a couple changes for the parties. Depending on how tired everyone is. She’s a lot of other things going on this weekend – lunches, brunches, parties. Tomorrow we have fittings. Now it’s probably 12 to 14 looks. Everyone was calling me saying, “Her SAG dress was her Oscars dress, you should have held it!” I said, “NOPE!”

You guys must be totally jived by the kind of fashion press you’ve gotten.

Oh yeah, it’s great. But it goes back to [the fact that] she makes the clothes fall in love with her. Everyone does these stoic moments on the carpet. Cynthia’s actually having a great time! I think that amplifies the visual for her right now. But she herself is very subtle and easy And I think that’s the perfect balance. The quiet personality and the big clothes is a beautiful balance.

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