I was first enraptured by actress Cynthia Erivo while watching HBO’s The Outsider. She has a way about her, not to mention a talent, that immediately transfixes you. Even without saying a word, her onscreen presence commands you to stop what you’re doing, watch, and listen . . . just in case she does. Erivo’s red carpet presence is very much like that. She wears couture gowns from the likes of Valentino, Gucci, and Versace that dropped jaws when — and if — they hit the runway (of course, some are custom). But somehow, when Cynthia carries these dresses out to the red carpet, your jaw drops even further.

“[Cynthia] allows me to just be a creative and truly never says no to a look!”

It’s her confidence, really — both in herself and in her stylist Jason Bolden, who has been working with the star since October 2019. “I love creating with Cynthia! She allows me to just be a creative and truly never says no to a look! A True Fashion Darling!” Jason told me via DM. Knowing he’s the mastermind behind some of her most avant-garde, groundbreaking looks is just too cool, but also sort of expected. Bolden works with Yara Shahidi, Storm Reid, Ava DuVernay, Alicia Keys, Sabrina Carpenter, Sasha Blane, Taraji P. Henson, Jaden Smith, Winnie Harlow, and most recently added to the lineup, famous inaugural poet Amanda Gorman. Jason does not play coy when it comes to sharing details about his clients’ looks. He is quick to confirm dressings and share the backstories behind his work, even revealing garments that didn’t make it to the red carpet but had their moment behind-the-scenes on Instagram.

It is with someone like Erivo (who is also an incredible singer and will be portraying Aretha Franklin in the upcoming limited series Genius: Aretha) that Jason is able to do his best work and try new things. It is clear that all of Cynthia’s most memorable fashion moments were born out of pure imagination, taking shape as she put on electrifying colors and stepped into unconventional silhouettes. And though they were very much made for uplifting Cynthia, they were also uplifting for the people.

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