Skip to main content

Meet Jessie Jamz, the Stylist Behind Ashton Sanders's Ascent into Menswear Stardom

With a Calvin Klein campaign already under his belt, the 'Moonlight' actor is poised to become a #menswear icon.
Photo: Kevork Djansezian/Getty Images

Photo: Kevork Djansezian/Getty Images

"Who is you, Chiron?" is one of the main questions posed in this year's "Best Picture" winner at the 89th Annual Academy Awards, "Moonlight." But the morning after the historic victory, the question was turned into a meme of sorts. "Who is you Chiron?!" GIPHY culture editor Jasmyn Lawson wrote on Twitter, captioning a gif of Chiron actor Ashton Sanders posing for photos at Vanity Fair's Oscars after party. In about a second of what Lawson describes to be unabashed black boy joy, Sanders shifts his weight, adjusts his kilt and takes off a pair of shades; it was, as they say, "a moment."

"All day he had been telling me about this kilt he'd just got because he'd been filming in Chicago," stylist Jessie Jamz told Fashionista over the phone last week about how the look came together. Jamz, who worked with Sanders for the entirety of his "Moonlight" press tour, continued: "After they won the Oscar, he was like, 'Where is my kilt, where is my kilt?!' I was like, 'Ashton we have to clear this,' because he was wearing Calvin Klein. I didn't want [the brand] to get bummed if we were mixing and matching."

Indeed, he had been wearing a double-breasted wool suit designed by Raf Simons for Calvin Klein. The three actors who played Chiron (as well as Naomie Harris) were wearing Simons's designs as a part of a meaningful bit of support the brand was showing to the film. But after a quick approval process — a CK representative was conveniently staying in the next room — Sanders swapped out his pants for the Fear of God kilt and threw on a pair of Vans with white socks at Jamz's suggestion. Right before they walked out of the hotel room where they had regrouped after the awards, there was another addition.

"He said, 'I need to wear my fur', and I told him, 'It's too much,'" Jamz confessed. "But then we looked in the mirror and it was like, 'Actually, no, this looks perfect.'" That collaborative styling process is indicative of how the pair have worked together since they were connected on a shoot for Ladygunn magazine late last year. And with Sanders's own personal style — as well as Jamz's outsider approach to the work as integral components — that process has turned out some eye-catching results.

The 31-year-old Jamz never planned for a career in fashion; she initially studied painting at the San Francisco Art Institute, but at the last minute switched up and got a second degree in graphic based design. It was this latter degree that ended up bagging her a job at Ed Hardy. "Back then I thought, 'This is so cool; I'm really in fashion now,'" Jamz explained. "I didn't know anything." That role turned into the job of jacket designer when Jamz's supervisor was fired. Google searches helped her "fake it 'til she made it" in the position, before she left to start consulting with smaller brands and designing her own pieces.

"I got in with this super-cool group of kids that were designers and stylists and other creatives," Jamz explained, clarifying that these weren't the Hollywood, celebrity stylist types. "I started going on set with them, styling my own designs, and from there I found out it was way cooler." So, she quit designing and in 2009 made the switch to styling. The best way to kick-start her career? Accept all jobs.

"I started saying yes to everything," Jamz explained. "It's for free? I'll do it. You need an assistant on set? I'll do it. You want me to style an ad campaign? I'll do it." That attitude turned into consistent work for ad agencies like 72andSunny working on projects for everyone from Disney to New Balance and Coors. Between it all, she worked on editorials and projects like music video shoots whenever she had the time. It was on one of these projects that she met Sanders.

"Ashton is my only 'celebrity styling' client," Jamz revealed. "My friend Shanna Fisher, a photographer, hit me up and was like, 'I'm doing this shoot for Ladygunn — it's unpaid. It's this kid in this movie that's going to come out. You may not have heard of him but it should be cool." Since Jamz had the day off, she decided to go ahead and book the gig. It took until the day before for reservations to arise.

Scroll to Continue

Recommended Articles

"I remember telling my boyfriend, 'Oh shit I'm really nervous,'" Jamz said. "I pulled gold bell-bottom women's pants. He's either going to be super-down or not into it." Thankfully he was, with the crew laughing the entire shoot. About a week later, Sanders reached out to Jamz for help on getting a look for InStyle's Golden Globes party (they ended up going with Public School) and the pair have worked together ever since, with Jamz juggling her ad work around the actor's red carpet appearances.

"[There was] a learning curve because some people are like, 'You have to wear head to toe,'" Jamz explained, citing the mandate that some brands will only loan pieces if they are styled exclusively with other pieces from the label. "We realized that it kind of confined us and was not something that either of us are really happy with. We decided early that if a designer isn't going to let us be as free, we don't have to work with a label just because it's a label."

"We mix high and low," Jamz continued, and has worked with brands like Valentino, Louis Vuitton and Saint Laurent on Ashton's behalf. "We'll get the Tiger of Sweden look for the SAG Awards and throw, like, $2 shades on him from the liquor store." It's that style that has caught the industry's eye, with brands like Alexander Wang reaching out, as well as the managers of other talent that hope to look like Sanders.

But even if Jamz does take on other celebrity clients — she contends she'll only do it if there's a genuine connection — they aren't likely to evoke the exact same look, as Sanders truly is a collaborator. "Ashton and I are in constant communication if we see something cool," Jamz explained, tossing out a litany of things that pique their interest: turtlenecks, mod styles, Andre 3000 and the 1960s among them. "If we see an ad or we're looking at the runway shows, we send photos to each other. Today I just got an email from someone who makes kimonos and I sent him some pictures and got his thoughts."

The result is true style, an amalgamation of what the pair have seen, refocused through their own, unique lenses. And ever since that first look, it's been not only a success in the press, but for Sanders and Jamz themselves.

"It was this camo Public School look," Jamz explained of that Golden Globes party 'fit. "I pulled that and Topman as a backup. He just looked so sick. But then there's just so much second-guessing on my part as he's walking out the door; basically I just send him off and sweat and look at my phone and get nervous. What if someone's like, 'What did he do?!'"

Fortunately, that fear has been unfounded thus far. "I remember the first text — I hadn't heard from him," Jamz continued. "Images came out on Getty, and I was thinking 'He's not happy, what did I do?' At 1 a.m., I get a text that's like 'Everybody loved it, I felt like a king!'"

And that, that's who Chiron is.

Want the latest fashion industry news first? Sign up for our daily newsletter.