Tonight, Roach will be the first recipient of the Council of Fashion Designers of America’s first ever Stylist of the Year award — his second major professional accolade in two months. (At the end of September, he 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 their “Most Powerful Stylists,” a title he took again in 2022.

“I’m a bit nervous, I think it’s too close to me,” he told CNN Style in a phone interview ahead of the CFDA award 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 so humbled, sincerely, but I gotta go to work.'”

Anya Taylor-Joy attends the LA premiere of “Emma” in February 2020. Credit: Jon Kopaloff/Getty Images North America/Getty Images

Roach and Zendaya attend the Valentino womenswear Spring-Summer 2023 show during Paris Fashion Week on October 2. Credit: Pascal Le Segretain/Getty Images Europe/Getty Images

His career is intrinsically entwined with the Emmy-winning actor, who he affectionately dubs his “annoying little sister.” The pair 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 styling. “I worked really hard to figure out the ins and outs 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 in 2021 made history as the youngest recipient of the CFDA’s Fashion Icon award — has ever worked with. “We kind of grew up together, and we built our careers together,” said Roach. “We’re still working together now and we’ll probably be working together for the next 30 years if we choose to. Also in a way, we became this blueprint for what people want a talent and stylist relationship to look like, which is a beautiful thing.”

Together, they have built something of a fashion empire. Across numerous Met Gala looks, including a Joan of Arc-inspired look featuring a custom Versace dress and chainmail for the event’s “Heavenly Bodies” theme in 2018, and subversive red carpet moments such as the hot pink Tom Ford chrome breastplate worn at the 2020 Critics Choice awards, the duo’s sartorial portfolio is as daring as it is successful.

To create Zendaya’s “Dune” press tour outfits Roach relied entirely on her narration of the film. “All her clothes were inspired by the movie, but I didn’t see it until Venice. So it was just her being very descriptive,” he said. According to Roach, Zendaya had selected the headline-stealing leather bodycon Balmain gown she wore to the film’s Venice Film Festival premiere two years earlier at the Fall-Winter 2020 Ready-to-Wear shows in Paris. “When that collection walked, she just said ‘This is very Dune,’ and I reached out to Olivier and his team.”

Ariana Grande attends the 62nd Grammy awards in January 2020. Credit: Steve Granitz/WireImage/WireImage

“I think that I am definitely a benefactor of social media,” said Roach, though he maintains virality is not something he consciously thinks about. “Sometimes we get caught in (thinking) you’re only as good as your last look,” he added. “There is a mental pressure to (not only) be successful but remain successful and relevant and do things which attract new people to wanting to work with you… It’s not just finding the prettiest dress.”

Zendaya walks the red carpet ahead of the ‘Dune’ premiere at the Venice Film Festival on September 3, 2021. Credit: P. Lehman/Future Publishing/Getty Images

Many might find the limelight daunting, but the obligation Roach feels towards improving representation in fashion is greater. ” I didn’t have any reference points for someone who looked like me, being where I’m from,” he said. “I was a little poor Black boy from the Southside of Chicago, so now little Black boys from where I’m from can say, ‘Well Law became successful.'”

With the awards beginning to pile up and much of Hollywood on speed dial, a natural question might be who is top on Roach’s red carpet wish list? Aside from a quick lamentation about never being able to dress Prince, the powerhouse’s answer is decidedly simple: “I just wake up every morning grateful that I still have a f***ing job.”