Leah Dolan, CNN

Even if you don’t know Law Roach’s face, you will have seen his work — whether you’ve picked up a fashion magazine in recent years or populated your Instagram feed with A-listers. Think of Zendaya’s 2015 Oscars outfit — a delicate white satin Vivienne Westwood dress offset by a cascade of brunette dreadlocks, the response to which prompted a conversation on discrimination towards Black hair — or the slate-gray, 20 foot-wide Giambattista Valli tulle dress Ariana Grande wore to the 2020 Grammys, or the vintage Bob Mackie wedding dress worn by Anya-Taylor Joy to the premiere of ‘Emma’ that same year. These enduring looks, to name just a few, are the work of Roach, the Chicago-born stylist who has found a knack for engineering fashion moments that cut through the noise of a typical red carpet.

On Monday night, Roach received 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.

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“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.'”

That’s a diligence that could be traced back to Roach’s humble beginnings in retail. After selling secondhand pieces out of his car to friends, he opened a vintage store, Deliciously Vintage, in Halstead, Chicago. He was first exposed to styling as a career after a serendipitous visit from Kanye West in 2009 landed the store coverage on TMZ. “We started receiving all these calls from stylists and it was all around the world. New York, L.A., London or Paris. I was just so impressed that so many people had this job.”

Soon after, he committed to a strategy of bluffing and self-belief. “It was literally just fake it ’till you make it,” he said. “When I met people that’s what I would say. I would be like, ‘I’m a stylist.'” Today, there’s no faking it. Roach now boasts over 1.2 million followers on Instagram and has a team of six assistants in the US and Europe to help manage his formidable client roster, which includes Grande, Taylor-Joy, Bella Hadid, Megan Thee Stallion, Keke Palmer and, of course, Zendaya.

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.”

Though fleeting, the right viral moment can wield powerful influence — a trend in social media (and beyond) that Roach has often been able to harness. In 2016, a street style snap of his client Celine Dion wearing an exquisitely self-referential Titanic-themed Vetements hoodie rejuvenated the singer’s sartorial relevance overnight. (Dion’s song “My Heart Will Go On” was the main soundtrack to James Cameron’s 1997 film.) She is now widely-viewed as a playful fashion mainstay.

“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.”

While his job could have easily seen him left behind-the-scenes, Roach himself has become a celebrity in his own right. He previously served as a judge on the “America’s Next Top Model” reboot, and is currently on the judging panel for HBO Max show “Legendary,” where his critiques and commentary are just that. (HBO and HBO Max are both owned by CNN’s parent company, Warner Bros. Discovery.)

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.”

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