Michael Stipe Reviews His 35 Greatest Fits: “This Was the F***ing Coolest Jacket on Earth”

A conversation about clothes with the former R.E.M. frontman turned visual artist and Saint Laurent campaign star, who as it turns out, can remember almost everything about every outfit he's ever worn.
Michael Stipe Reviews His 35 Greatest Fits “This Was the Fing Coolest Jacket on Earth”

Over time, as Stipe became more famous—and at least relatively more at ease in the public eye—he started dressing with more intention. One of his earliest sartorial mentors was Jeremy Ayers, an Athens-born writer, photographer and musician who Stipe describes as “one of the earliest loves of my life.” After leaving Georgia for New York, Ayers had become part of the scene around Andy Warhol’s Factory, where he was known as “Sylva Thinn.”

“He dressed as a woman,” Stipe said, “and presented as a woman most of the time that he was there with Andy. But when he moved back to Georgia, he just would dress like a scarecrow. He would go thrift shopping and pull all these really classic looks together, but he always had something that was off, or amiss. I took that and ran with it and kind of made it my own thing.

“I wanted, as a teenager, to be like this hairless, androgynous David Bowie type,” Stipe said, “and I'm exactly the opposite of that. I've got bad skin and I've got funny hair. I always did. Courtney Love and I talked about this a lot with each other, early in our friendship. We both were just from the island of broken toys, and we would never fit into that look that we wanted to fit into. If I was trying to wear something that was completely tailored and gorgeous, I looked ridiculous in it. So if it was a little bit off, it always looked a bit better. Rumpled is better. I have to wear things that are extremely tailored and then they fall apart while they're on me, and that's a good look.”

A few days after the Saint Laurent billboards debuted in New York, Stipe dialed in to a FaceTime call to talk about the evolution of his style and annotate some images of his many iconic looks; he’d been staying in Georgia, in a house he bought when he was twenty-five, and occasionally he’d jump up from his seat, disappear into another room, and return with some priceless vintage piece from his personal archives. What was supposed to be a brief conversation ended up exceeding 90 minutes; Stipe is a visual learner, he explained, “so I see the picture, the clothes, and I’m instantly reminded of the era, of the moment.”