I don't know how it works for other style icons—guys who have hit singles stretching back into their teens, who have acting careers, who are mixing and sampling with Timbaland and Rick Rubin, and doing duets with the likes of Madonna—but when Justin Timberlake gets dressed in the morning, he does not think about how he looks. Really. He swears. Or so he claims today at San Diego's Torrey Pines Golf Course, where he is planning to respond to a challenge set by Tiger Woods, who declared that no amateur golfer could beat 100 on a U.S. Open course. (Timberlake ends up breaking 100—and possibly scores even better with his black fedora.) "Honestly, I don't walk out of my house thinking, Man, I hope somebody thinks this looks cool!" he says. "There's some stuff I wear that people think is not cool." Could he be referring to the ostrich-leather pants he once wore during his days with *NSYNC? "I think that so much is how you carry it and how you feel in it," he continues. "The same way that golfers dress differently now because of Tiger Woods. I don't think they are conscious of it. They are just like, 'This is what I feel right in.' It's a state of mind."
It is the Timberlake state of mind, in other words, which is intense but relaxed. He ticks through a list of his idols: Stevie Wonder, the Beatles, Prince, Brian Wilson. "All those people, they were just doing what they did," he says. "They were not planning on becoming iconic or a photo image in people's minds. You think of Stevie, you think of the glasses, the braids, and his voice. You think of the Beatles, you think mop-top, haircut, suits. You think of Prince, you think purple. You think of Marvin Gaye, you think skullcap with a peacoat. I don't think you plan stuff like that. You sort of just are who you are."
Given that he has sold close to 18 million albums, you would have to be living in a cave without an Internet connection to not know who Justin Timberlake is. His most recent album, 2006's FutureSex/LoveSounds, had six Top 20 hits. Lately, Timberlake—JT for short—has been in so many movies that you would be forgiven for thinking he was a rising actor with a music career on the side. Over the summer he was in Mike Myers's Love Guru, part of a comedy run that started with Andy Samberg's Saturday Night Live short film Dick in a Box, a hilarious parody of early-nineties R&B videos that won an Emmy and is still a YouTube hit. Prior to that, JT was impressively gritty in Nick Cassavetes's Alpha Dog, a gang story, and impressively kids-y in Shrek the Third, in which he was the voice of a young King Arthur, acting with his former girlfriend, Cameron Diaz. (Jessica Biel, his current amour, is somewhere in the vicinity of the golf course today.)
Now 27, Timberlake began his career as a preteen Star Search contestant at the Grand Ole Opry in his home state of Tennessee. By ten, he had landed a gig with The Mickey Mouse Club, alongside co-Mouseketeers Britney Spears and Christina Aguilera. He graduated to *NSYNC at the height of the boy-band era, then went solo in 2002, the CD Justified legitimizing him as an R&B artist. He dressed at the time in baggy leather pants, T-shirts, and fedoras, and later moved on to suits with sneakers. As Sinatra allegedly took care never to lose the crease of his pants, so Timberlake adjusted his hem to make his suits high-top compatible. "It's all about how the pants hang, man," he says. He was banned from the Grammys after an infamous "wardrobe malfunction" at the 2004 Super Bowl got him and Janet Jackson in trouble with the censors, but he apologized, as requested, and in turn was permitted to accept numerous awards, including Best Male Pop Vocal Performance for "Cry Me a River."
In 2005, with the help of his childhood friend Trace Ayala, Timberlake launched a fashion line, William Rast. The moniker was concocted from the first and last names of Timberlake's and Ayala's grandfathers, who also grew up in Tennessee together. Timberlake and Ayala started small, focusing on denim, but this fall they're taking things to the next level with the help of Johan and Marcella Lindeberg, the husband-and-wife team behind the unsung hipster label J. Lindeberg. A fan of the brand, Timberlake arranged a meeting with the duo in San Diego last year and subsequently hired them as designers. "We really connected," Johan Lindeberg says.
The plan was to build a line that wasn't based on Timberlake but was nonetheless connected to him aesthetically—or in Johan Lindeberg's words, "to go deep within the roots of Tennessee and try to meld them together with the Hollywood showman that he is." Timberlake sent them pictures of vintage Gibson guitars, his favorite old Mercedes coupe, and the Tennessee countryside. "I'd say, 'This is where William Rast should be walking,' " Timberlake recalls. "We've got to the point where William Rast is a character."
The fall ad campaign, released this month, features Timberlake and has a Bonnie and Clyde feel. The women's line is not too dressy, while the men's feels a little bit Grand Ole Opry, a little bit Hollywood Bowl. "I'd describe it as Southern heritage meets forward European innovation," says Timberlake. "It's me in Europe. It's basically me and Trace mixed with Johan."
Technically, the two friends started designing back when Ayala made a pair of jeans for Timberlake in the *NSYNC days, and Timberlake can remember spray-painting vintage Air Jordans and shaving a beehive design into Ayala's hair. "We just didn't care," Timberlake says. "We kind of still don't." When they moved to L.A. together, they continued to experiment with fashion. "It's funny, I keep hearing Ashton Kutcher say how he was responsible for trucker caps," Timberlake says. "I've heard him make that statement before. Trace and I were wearing them when we were seventeen."
"I gotta be completely honest," says Ayala. "I think we did start the trucker hat. I came up with it—and Justin made it cool."
Ayala sees a link between Timberlake's fashion and his music, the suits that JT wore on the "FutureSex/LoveShow" world tour were an idea that surfaced in the studio. As Ayala remembers: "Justin said, 'You know what? If I was wearing a suit with this, then that would bring sexy back!' "
Not that he always wants to be bringing sexy back. In David LaChapelle's 2001 video for Elton John's "This Train Don't Stop There Anymore," Timberlake played Elton at the height of his flamboyance, when the artist was trapped by his fashion fame. It's a beautiful video, and Timberlake immersed himself in the cautionary role. "I play Elton at the height of the hoopla," Timberlake says, "and show how he sort of shied away from it. He just wanted to play his music, be who he was. He didn't want to be a crazy suit; he didn't want to be a pair of big glasses. He wanted to be Elton John. You know, the same way that I don't want to be Mr. Sexy Back forever. That's what he was feeling. He didn't want to be the Elton John who wears crazy outfits onstage. He wanted people to love his music. Obviously they did—and still do. But somehow fashion icons become a photo in people's minds." He pauses and shrugs. "I think sometimes people see me in a fedora, or in a suit and sneakers. You are locked in the photo. That's our day and age."