How Jason Bolden Went from Retail Jobs to the Oscars Red Carpet

When Jason Bolden draped a custom deep blue Alberta Ferretti gown on Taraji P. Henson for the 2017 Oscars, he felt like more than just her stylist. "It was that quintessential moment when I saw my mom, my sister, and my best friend come to life," he says. "The power in that moment and that look spoke to me on so many levels." That night, Henson was on the red carpet for the Academy-approved Hidden Figures, and the sought-after stylist had given the star (and her audience) a vision of elegance.

Beyond Henson, Bolden's styling roster includes names like Ava DuVernay, Janet Mock and Yara Shahidi -- a career trajectory that might not seem obvious for someone with his background. "It was tough for me," Bolden says of getting into the business. "I look at a lot of other people who came up through the ranks [in fashion], or grew up in a situation where their families were tied to something, and you realize it's all about proximity. I didn't have that."

Raised in St. Louis, Bolden got his start via retail and embarked on a path that didn't involve apprenticing in a typical manner. "I was learning so much being on the ground level with customers," Bolden says. "I was so close to the people who were really making the cool decisions." After interacting with consumer interests firsthand -- working for brands like Chloe, Louis Vuitton, and Gucci -- he helped cofound and curate The Garment Room, a New York-based vintage store.

It was in this role that Bolden increasingly developed celebrity connections which resulted in direct requests for his expertise. "I've been lucky in the sense that some of my biggest opportunities have just come to me; I haven't really had to seek them out. I started feeling like this was a career when I began getting phone calls and requests for me to do things," he says of fielding inquiries from leading women like Gabrielle Union and Henson. "[Styling] kind of chose me more than I chose it."

Since then, the women (and select men) of Bolden's talent catalogue have grown alongside him in their boldness. The precocious Shahidi, whom he calls the "voice of the planet right now," takes turns on the red carpet in brands like Off-White, Chanel, and Calvin Klein, but is constantly making headlines for her words on activism and politics. In the lead-up to the 2018 midterm elections, she helped organize summits and events to get more teens registered to vote. These are things Bolden has considered bigger than the garments he dresses her in: "The way that the looks land on Yara is always great, but we are always waiting to hear what she has to say," he says.

Bolden's ever-focused eye for fashion is a major asset, but it isn't the only one in his arsenal. Through JSN Studio, the company he owns and operates with his husband, Adair Curtis, he's not only dressing clients, but designing the spaces they live in, too. "I feel like it's a complete story," he says. "Like you see people in these really fabulous clothes, but where are they hanging it? Are they putting these Manolo [Blahniks] in this really bizarre situation?"

Bolden answers the interior design questions, while Curtis -- a former executive for hip-hop mogul Russell Simmons -- handles the business and architectural components. Their collaborative process will soon get the small screen treatment via a new, yet-to-be-named Netflix docuseries. Beyond their work, viewers will also get details on their enviable life together. "You have these two Black men who love each other and their careers are doing really well, but what does that really look like?" he says. "I personally know what it looks like for me because I live it, but I also look out sometimes and have to say, 'I don't see anything that mirrors myself and my husband.'" Now, everyone will get the chance.

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