Derek Roche, a Goldsboro, N.C. native, has been Diddy's personal stylist on and off for the past 11 years. The role has taken him around the world, styling the multihyphenate billionaire for boardroom meetings, meals, performances, shoots and red carpet events like the Met Gala. He's even been tasked with dressing the likes of Cassie and Nicki Minaj on occasion. The job is hectic, ever-changing and multifaceted, and it's brought the former Vibe market editor his own bit of notoriety, including a stint on Lifetime's "Million Dollar Shoppers" series. But, like any full-time gig worth having, it hasn't been without it's bumps.
"[About] five years ago, we were in Miami shooting the 'Dirty Money' video," Roche recently explained to Fashionista in Los Angeles, where he's currently based. "I'd pulled a purple jacket. We'd just come back from Glasgow, and Puff wanted a pair of glasses he wore there, and he wanted his shoes to match this jacket. I couldn't find find the glasses or the shoes and said, 'Puff I don't want to put a purple shoe with a purple jacket.' He didn't care. We got into this huge fight," he said. Roche stood his ground. "So, I left, and I was back in New York by the time they wrapped the video in Miami." Shortly after, the stylist resigned — marking the third time he would do so. After a year and a half of freelancing (mostly working with Ne-Yo), the pair reconciled and have reestablished their working relationship.
The youngest of four siblings and a self-professed "momma's boy," Roche enrolled at University of North Carolina-Greensboro after high school to study speech pathology, for no other reason than someone else he knew had done it before. "I went over to my teacher's house to study for finals or something and started talking to her daughter," he said. "She told me she was going to UNC-G and was studying speech pathology, so I said that's what I would do." A year into the program, he switched his major to textile design after finding that he enjoyed "making stuff to go out in." The summer before his senior year, as a requirement of his program, he completed an internship in Patricia Fields's office.
"That was my rite of passage,"he recalled of the time that saw him helping with samples as well as helping coordinate projects with the camps of Britney Spears, Mya, Eve and "Sex and the City." "I thought, 'I'm a professional now.'" But even with that feeling, Roche made a real effort to learn the ins and outs of the industry, carrying a notebook with him to write down the names of everyone he met. Later, he'd Google them to find out what they did.
After graduation, with $600 and a credit card, Roche moved himself into a "sight unseen" Brooklyn apartment with a friend. While the move was a big deal for the very family-oriented stylist, he understood the disadvantage he had getting into the industry. "I went to UNC-G which was a small art school, so I knew I couldn't compete with kids who went to Parsons, FIT and Central Saint Martins — you know, the 'Ivy League' of fashion schools," he said. "I knew I would have to do another internship, so I got one at Vibe in the fashion department under the fashion assistant." Fortuitously, his boss had also spent some time at UNC-G, which provided an instant connection.
After spending six months at Vibe while holding down gigs as both a bathroom attendant and a Gap employee to pay bills, he left, not seeing any room for promotion. Eventually, he found his way to a company that did production for American women's sportswear brands, but before he left, Michael Nash, then the fashion director of Vibe, gave him a bit of valuable help.
"I was telling him that I needed to make money and he gave me three people's names," Roche said. "He said, 'Text these three people, let them know I sent you and offer them your help if they are working on anything.'" One of those numbers called back, looking for an assistant to work on set at a photo shoot. Roche took a sick day at his full-time gig to make it work, and a few weeks later, he was hired as a fashion assistant working under Daniel Ou and Bruce Pask at Cargo, the short-lived men's version of Lucky. Two years later, he was called back to Vibe as the market editor in a role that saw him pulling product, styling celebrities and helping with in-book features.
And then came the opportunity with Diddy.
"The thing that's exciting is that [Diddy] is into fashion; he's into music; he's into art — he's a chameleon," Roche said. "What really excited me about the job was the uncertainty of tomorrow." He was recommended for the position by a friend who was interviewing for a job at Sean John; Roche went through a three-month interview process and ended up getting hired only because the first choice couldn't last after two weeks. "Things change minute by minute, day by day," he said. "I didn't know what I would need to do or where I would be, what city we were going to, what country we were going to." But four months in, that's exactly what ended up being the reason the pair first parted ways.
"I think it just burnt me out," Roche said of the role. "In editorial, there were hard dates to meet because of press deadlines. Here, everything was moment to moment, and I think it really threw me for a loop." He resigned to begin freelancing for the likes of W Magazine and Ralph Lauren before moving back to North Carolina to teach home economics to middle school students. But as the summer rolled around, Diddy's team reached out to have Roche help style the rapper for a European tour. He never went back to teaching.
Diddy's fast-paced lifestyle and non-sample size build means that he buys about 90 percent of his wardrobe, according to Roche's estimation. "The challenge is he's a billionaire in a board meeting one day, and then he's in Harlem [the next day] wearing something from Dapper Dan, and the next day I could have him in an H&M [jogger] and shoe moment and that will be fine," Roche said. "He's all about being appropriate. He doesn't wear the same thing over and over again, but he also references his roots from when he was producing and styling Jodeci or when he styled Mary J Blige — he's quick to remind me of that. It always keeps me on my toes." But that appropriateness also means that, at 47-years-old with six children, he's not likely to make the rounds in an unbuttoned Versace shirt and Gucci loafers like many top names in hip-hop and the affiliated industries do today.
The aforementioned Dapper Dan has become a secret weapon in Diddy's arsenal. "Dapper has never gone away for us, he's always been around," Roche said when asked about their work together, which would have started about half a decade after Dan's shop was closed. "I get texts from people all the time that need to get something made asking for Dapper's contact information. He's like the Wizard of Oz: If you don't know him and you don't know where the yellow brick road is, you can never get to him." According to Roche, the portfolio of work for Diddy goes far beyond the logo-heavy designs Dapper is known for, and spans suiting, shirting and even a recent velour suit that made it into Vogue.
With a team of designers like Dan and Diddy's other trusted stylists (like longtime collaborator Groovey Lew) by his side, Roche has been able to turn out something of a signature look that's as multifaceted as Diddy himself. Rising the ranks to become a celebrity stylist is a tall order on its own, but Roche has earned the stamp of approval of a man who was "friends with Donatella when supermodels were supermodels," put on the first nationally televised live fashion show in 2001 with his label Sean John and won a CFDA award for menswear in 2004. If anything deserves extra bragging rights, it's that.