Zendaya attends the Oscars on February 25, 2015 in Los Angeles Credit: Frazer Harrison/Getty Images North America/Getty Images
On Monday night, Roach received the first Stylist of the Year award from the Council of Fashion Designers of America, her second major professional award in two months. (In late September, she made the TIME100 Next list of emerging leaders shaping their industries.) Last year, Roach made history as the first black person to top The Hollywood Reporter’s annual ranking of its “Top Stylists powerful”, a title that was taken again in 2022.
“I’m a little nervous, I think it’s too close to me,” she told CNN Style in a phone interview before the CFDA awards ceremony. “I live in a bubble where my work is basically the most important thing. So I think I don’t really allow myself enough time to really understand how big these things are. It’s always, ‘Oh, I’m so grateful.’ I’m very humbled, honestly, but I have to go to work.”
Anya Taylor-Joy attends the premiere of ‘Emma’ in Los Angeles in February 2020. Credit: Jon Kopaloff/Getty Images North America/Getty Images
Roach and Zendaya attend the Valentino Spring-Summer 2023 womenswear show during Paris Fashion Week on October 2. Credit: Pascal Le Segretain/Getty Images Europe/Getty Images
Her career is intrinsically tied to the Emmy-winning actor, whom she affectionately calls her “annoying little sister.” The couple met when Zendaya was 14, during the first season of her Disney show “Shake it Up.” It was through their creative relationship that Roach says he began the real work of learning the day-to-day reality of celebrity style. “I worked really hard to figure out the pros and cons of being a stylist because I didn’t really have a mentor, I was never anyone’s assistant or an intern.”
Roach is the only stylist Zendaya, who made history in 2021 as the youngest winner of the CFDA’s Fashion Icon Award, has ever worked with. “We grew up together and built our careers together,” Roach said. “We’re still working together now and probably will be working together for the next 30 years if we choose to. We’ve also, in a way, become this model of what people want a talent-stylist relationship to look like, which is a beautiful thing.”
Together, they have built something of a fashion empire. Through numerous Met Gala looks, including a Joan of Arc-inspired look in a custom Versace dress and chainmail for the event’s “Heavenly Bodies” theme in 2018, and subversive moments from the red carpet like Tom Ford’s hot pink chrome breastplate worn at the 2020 Critics Choice Awards, the duo’s wardrobe is as bold as it is successful.
To create the outfits for Zendaya’s “Dune” press tour, Roach relied entirely on her narration from the film. “All her clothes were inspired by the film, but I didn’t see them until Venice. So it was that she was very descriptive,” he said. According to Roach, Zendaya had selected the skin-tight Balmain leather dress she wore to the film’s premiere at the Venice Film Festival two years earlier at the fall-winter 2020 ready-to-wear shows in Paris. “When she walked this collection, she just said, ‘This is very Dune,’ and I contacted Olivier and his team.”
Ariana Grande attends the 62nd Annual Grammy Awards in January 2020. Credit: Steve Granitz/WireImage/WireImage
“I think I’m definitely a social media benefactor,” Roach said, though he maintains that virality isn’t something he consciously thinks about. “Sometimes we get caught (thinking) you’re only as good as your last look,” she added. “There’s a mental pressure to (not only) be successful, but to stay relevant and do things that will attract new people to want to work with you… It’s not just about finding the prettiest dress.”
Zendaya walks the red carpet before the premiere of “Dune” at the Venice Film Festival on September 3, 2021. Credit: P. Lehman/Future Publishing/Getty Images
Many may find the spotlight disconcerting, but the obligation Roach feels to improve representation in fashion is greater. “I had no reference for someone who looked like me, being where I’m from,” he said. “I was a poor black kid from the South Side of Chicago, so now black boys where I’m from can say, ‘Well Law was successful.'”
With the awards starting to roll in and much of Hollywood on speed dial, a natural question might be who’s top on Roach’s red carpet wish list? Aside from a quick lament about never being able to dress Prince, the powerhouse’s response is decidedly simple: “I just wake up every morning grateful that I still have a horrible job.”