“I actually think they started doing it to prove a point,” says Leslie Fremar, a stylist who has dressed Jimmy Fallon and Johnny Knoxville, and who believes that grunge antiheroes like Kurt Cobain set the down-and-out dress code for today’s stars with their reverse-chic posturing. Tim Gunn suggests that it’s a matter of status. “The higher up you are in the celebrity hierarchy,” he says, “the more qualified you are not to dress up.” By this logic, dressing up looks like striving, like you haven’t quite arrived. The funny thing is that all these men carefully rumpling their shirts and hair spend as much time on their appearance as the ones in suits and ties. “You get these guys that act like they don’t care how they look,” says Cher Coulter, an L.A.-based stylist who dresses Orlando Bloom, Eric Bana, and Colin Farrell. “But you know what? They do. Or else they would just wear the suit their publicist tells them to. Sometimes I feel like I’m asking for blood to just get them to put a vest on. They want to just look like a dude and be like, ‘I’m real.’” Many stars are, of course, willing to strip off the couchwear and shrug into finery donated by a designer. And some, like Bloom and Gyllenhaal, seem to enjoy dressing up for big events; Lauryn Flynn, director of celebrity services at Calvin Klein, reports that Terrence Howard spends hours choosing accessories. Could it be that the pendulum is starting to swing back?
“The jeans-and-T-shirt look has become the establishment,” says Thom Browne, the meticulous suitmaker who won this year’s CFDA menswear award. Today’s real rebels, he says, are the ones in suits. Coulter thinks that the music scene is having an influence again: “Look at what all the cool British bands are wearing now.” Even Dolce & Gabbana, the designers who once touted shredded denim as formalwear, are putting their celebrity clients in basic black suits. “I’m 47 years old,” Domenico Dolce says. “I want to dress like a man, not a boy.”