Perhaps once a decade, an unconventionally beautiful (read: not thin) artist exerts such an irresistible magnetism as to blow the deadbolts off of the fashion world and disrupt production of the beauty myth. In the early 1990s, the comely voluptuousness of celebrity makeup artist Sharon “Mama Makeup” Gault inspired designers to push her from backstage to the catwalk. The immortal look of club icon Leigh Bowery—with his form-malforming, anthropoid Jayne Mansfield-in-sequined-ski- mask garments—made such a deep impression on fashion that his unlikely influence is still occasionally seen in Missy Elliot videos, and on the runways of Gareth Pugh.

He sits alone, slouching on the phone at an outdoor table at the Maritime Hotel, in Manhattan’s Chelsea district. All grown up now, a little scruffy around the edges. Not in a bad way, just not trying to look perfect, wearing the kind of canvas jacket and jeans you might see on a handyman-style hipster.

Matt Dillon has been a movie star since 1979, when a film director spotted the 14-year-old, black Irish altar boy from New Rochelle cutting class one day, and promptly cast him in the anarchy-in-suburbia, teen angst drama Over the Edge.

Celebrity stylist Rachel Zoe has survived media beatings of a viciousness ordinarily reserved for bottomless heiresses and ex-Mouseketeers. A-list clients (“Zoe-bots,” if you’re nasty) catapulted Zoe, 36, to infamy. But the tabloids were also the nexus point between high fashion and low culture (Lindsay lurches into paparazzi-fire with handbag; handbag sells out globally within 40 minutes). Zoe capitalized on the frenzy with the creation of her own signature brand. Here, the Long Island sunglasses come off and it becomes clear that there is more to Zoe than hippie headscarves, eating disorders and caftans.