Nick Wooster: Style Becomes Him

Photography by Sophy Holland

For a man with almost 500,000 followers on Instagram, and whose Wikipedia designation is "street style icon," Nickelson Wooster is remarkably humble. "I'm just this kid from Kansas who happened to obsess about clothes, and the fact that I can actually make a living based on that is the most gob-smacking thing in life," he says. "Fran Lebowitz says she's not afraid of anything except for writing. For me it's the opposite: I'm afraid of everything, and the only thing I'm fearless about is getting dressed."

Wooster, an early riser who needs three hours of cigarettes and iced coffee before he can think about leaving home, compares his instinct for style to being left-handed. "I can remember being in pre-kindergarten and having a meltdown about certain clothes that I would and wouldn't wear," he recalls. "I would say, 'I don't like the sleeve on this T-shirt,' and my mom would look at me like I had seven heads, like, What the fuck are you talking about? It's a short-sleeve T-shirt."

Looking back, Wooster is aware that his passion for fashion also served as a camouflage -- for his insecurities about his height, his looks, his sexual orientation. Clothing, he realized, could take care of all of that. As a teenager, he took his cues from his stockbroker grandfather, who wore suits and took him on his first trip to Macy's in Wichita. It was a revelation. By 16, he was working in a local specialty store, and apart from a slight detour as a journalism and advertising student, fashion has been his metier ever since.

His resume is a who's who of major brands, from retailers such as Bergdorf Goodman and Neiman Marcus to designers like John Bartlett and Thom Browne. He is currently curating the Cadillac Capsule Collection, a selection of 15 looks for the fall.

His arrival in New York on January 8, 1983, coincided with a low point for the city's gay community. "I arrived to stay with my aunt and uncle on a Saturday, and on Sunday morning they were passing out sections of the paper," he recalls. "The magazine came to me, and the cover story was about AIDS." The story stopped Wooster in his tracks. "It scared the shit out of me, and I can't believe I'm here and HIV-negative, because I shouldn't be," he says. "I did it all -- I would be at Paradise Garage, at Palladium, at Area, at the Anvil, you name it. Getting high was how I dealt with the '80s."

Although he laughs off any suggestion that he's a role model, Wooster, sober now for 20 years, feels a responsibility to show that there is more to life than being high. "I'm amazed now to see how many guys get sober in their 20s, when I was certainly qualified at that point," he says. "I was just never interested -- I couldn't do it." He is bashful about his huge social media following, but aware, too, that it helps keep him relevant -- and employed.

"Why weren't they taking pictures of me when I was cute?" he jokes. "Why would a vertically challenged, not fit, 55-year-old person be of interest to anyone?" He laughs. "Whatever it is, I hope it sticks!"