It's 7:50 a.m. on a brisk December morning at Sherwood Country Club just west of L.A., and Justin Timberlake is not only awake; the dude is looking crisp. Like out-of-the-box crisp. Like he could go ahead, right this minute, and tee it up in front of a half-dozen television cameras: pressed black slacks, a slim white golf shirt, and a black-gray-and-white argyle sweater vest.
The golf—and tee time—was his idea. As with a lot of things in his life (music career, acting career, ascendant clothing line), Timberlake takes the game seriously. He started playing in earnest about five years ago and has been working with Butch Harmon, Tiger Woods's former coach, for the past year and a half. He's now a 6-handicapper.
For those of you who don't spend your Saturdays obsessing about your swing plane, that means he's able to step up to the first tee this morning—without any time on the driving range—and yoke it 280 yards down the center of the fairway with a soft, arcing draw.
No, life isn't fair.
But at least Timberlake—with 16 million solo albums sold and Jessical Biel to his credit—isn't one to rub your half-awake face in it. In fact, he couldn't be more laid-back this morning. No entourage, no assistant, no wraparound shades. Just he and Nick the caddie (who is rocking a pair of wraparounds, as well as a mustache and a mess of shaggy hair; he looks like a spot-on extra from Almost Famous).
Ostensibly, we're here to talk about fashion and design and all those other subjects that have catapulted Timberlake to the front of our Most Stylish Men in America issue. Which is all well and good with him. But for a guy with so much filtering through his career mixing board, he's hardly in a rush. "Dude, we can do the interview now, while we're playing, or we can do it later. We can grab some lunch. Whatever you want. Let's just play some golf, man."
So we do play. And Nick and I watch as Timberlake hits every fairway but one on the front nine, for a 42 at the turn. He tightens up his short game on the back, firing at pins, zipping balls backward on the greens like the pros do, and (finally) draining a few key putts, for seven straight pars and a final score of 80.
All the while, there's chatter about fedoras and three-piece suits and his clothing line William Rast—and why we included Timberlake on our list in the first place: not because of some effortless way he dresses or comports himself but because of the way he works at his style. Timberlake has a knack for targeting trends just before they crest. He might not spark them, but he's the guy who broadcasts them—whom we point to for making, say, hats popular again, or for making suits look like they were meant to be worn with sneakers, or for wearing a beard that's not quite a beard per se but is pretty much what every guy at the club wears these days.
His impact is undeniable, as is his willingness to take risks. He's the guy who rocks the sweater vest off the course ("definitely—but not argyle; a solid-color one, usually with a T-shirt underneath"); the tie with a leather jacket ("but a really good leather jacket—really sleek and clean looking").
On the seventh fairway, while he reaches for a 7-iron, I ask if his girlfriend ever gives him a thumbs-up or -down on his outfits before he leaves the house. Timberlake shoots an "Are you kidding me?" look and then answers a definitive no. At which point Nick the caddie jumps in: "Dude, he's the fucking King of Pop! He can wear whatever he wants to wear. If he wants to rock sandals with socks, a week later everyone in L.A. is going to be wearing sandals with socks!"
Well, we hope not, but point taken. Timberlake is like an athlete entering his prime—firing on all cylinders, nailing everything. Sure, he has made his mistakes (acid-wash denim suit, white-boy Jheri curls, razor-beard-goatee unit), but those days are behind him. He's the guy we end up dressing like a year after he's adopted the look. And that's why he's kicking off our list—and why we're here to glean from him the kinds of style tips, secrets, and rules that we non-Grammy-award-winning, mere mortal 14-handicappers can learn from.
1. Rock Your Roots
If you want to know where Timberlake gets his style DNA, you don't have to look far. His stepfather, Paul Harless, a recently retired banker, set the mold.
"Nobody dresses like my dad,"1 Timberlake says. "When he worked at the bank, he looked like Richard Gere in Gigolo. And he would do it all the night before, laying out the suit he'd wear the next day. Even on weekends, if he had to go into the office, he'd wear a trouser pant with a V-neck sweater and tie. And I was like, I want to dress like that! He was just so cool.
"When he'd get his pants hemmed, he'd ask for them to be slightly longer in the front, because he wanted them to bow. So when he walked, he had this Travolta thing going, where the pants would flop a little bit. And it was cool, man! Some days my mom would come get me out of school a little early, and we'd go meet my dad for lunch. And I remember him walking out of the bank, and with his pants it was like he was gliding down the sidewalk."2
2. Make Your Mother Proud
"You want something to eat or drink? Want to hit some balls before we head out? You wanna go off the first tee or the tenth?"
Play golf with Timberlake and what you notice more than his threads or his golf-school-honed backswing are his manners. He is unfailingly polite and courteous. Not in an obsequious way but in a matter-of-fact, this-kid-was-raised-right sort of way.
Credit his mother, Lynn Harless.3
"She always said to me, 'Just because you do this one thing really, really well, it doesn't make you better at everything. It doesn't make you a better person.'
"The values my mother taught me were like, If you're going to do something, don't half-ass it. I remember her literally saying that to me. Like the first time I ever heard the term half-ass was coming from my mother's lips. I was probably 8 or 9. If you're going to do something, go ahead and throw 115 percent at it, and if you get 100 percent back, well, there you go—you're perfect."
3. Never—and We Mean Never—Dress Yourself Around a Hat
Whether he likes it or not, Timberlake is the guy we think of when we consider the resurgent popularity of old-school hats, like fedoras, trilbies, and porkpies. He realizes this is not always such a good thing.
"I do like ats. But I specifically tossed out some fedoras recently. Like this charity event I went to last night, there was this dude who was so particularly wearing his hat back with some hair sticking out in the front, like he was trying to be in the Brat Pack. He looked like Rob Lowe. I was like, Why? How much time did you take on that? It looked like everything in his outfit revolved around the hat.
"The thing is, you don't put your underwear and socks on, then a hat, and then get dressed. And subconsciously people do that. They're like, 'I'm gonna fucking wear this hat today! I just bought it, and I'm gonna rock this hat to the bar tonight! And I can't wear this leather jacket with the hat, because it doesn't look right, so I've got to wear this peacoat....' It's like, Dude, if it takes that much thought, start over."
4. When There's Work to Do, Make Sure You're Looking Good
Watch Timberlake's videos and you understand there's a point to how he dresses. He's a showman, in the most traditional sense of the word: He sings, he dances, he glides, he grooves. He's a physical4 dresser, like Gene Kelly or Sammy Davis. In the video for "SexyBack," he's tricked out in a black Dior suit, ruler-thin tie, and trim collar. But for the dance scene, it's a vest, Jesse James bandanna around the neck, and loose pants slung low on the hips. Clothes he can move in. Same as those three-piece suits he wore on tour, designed for him by Stefano Pilati of Yves Saint Laurent. The pants have a kick, a looseness to them. They're easy. Just like the shoes he wore onstage.
"Some guy came up to me and said, 'You single-handedly made it cool to wear sneakers with a suit!' I mean, I just put sneakers on because I couldn't dance in the shoes I had. I couldn't leap with just insoles and dress shoes. I would've hurt myself."
5. Know When to Take It Off
"I find that every year, I tend to look at my clothes and think, I just want to go more and more simple. Who was it who said—was it Lagerfeld?—before leaving the house, put everything on you want to, then take one thing off?"5
6. If You're Going to Do Something, Do It Right
When I first heard that Timberlake was launching William Rast, I rolled my eyes and thought, Of course, what musician doesn't have a clothing line these days?
"I knew that response was inevitable," Timberlake tells me, "but my buddy and I wanted to do it so bad, we were just like—screw it."
Timberlake eventually approached Johan Lindeberg, who launched the fashion-and-golf label J.Lindeberg, to take the design reins. Lindeberg, however, was skeptical.
"Obviously, I wanted to meet Justin," Lindeberg says. "He's one of the few stars out there who understands tailoring and golf. But to work on a celebrity clothing brand, I wasn't so keen. I wanted to know that he had the passion and strength to make it work."
Timberlake was determined to convince him he was in it for real and set a meeting with Lindeberg. Three hours later, Lindeberg signed on and now, with his wife, Marcella, is overseeing a mix of skinny jeans, vests, white tux jackets, graphic T-shirts—the kind of clothes Timberlake himself would wear. Modern Americana is the phrase that Timberlake and Lindeberg like to bandy about.
"Johan and I are like family now," Timberlake says. "I always send him stuff—you know: 'Hey, watch this movie.' 'Hey, listen to this song.' We never say, 'Hey, look at that shirt! We need to make something like that shirt!' It's about creating a lifestyle."
And if all goes as planned, according to the two of them, a lifestyle that extends beyond Timberlake's last name.
"I think the brand, it needs to be bigger than its founder," Lindeberg says. "Ralph Lauren the brand, for instance, is bigger than Ralph Lauren the person. That's when you know you're succeeded with something."
7. Find Your Inspiration
"Who's a style icon? Kate Moss. She looks good in anything. She would look good in one of your T-shirts, in her T-shirt, in a man's suit, in a huge gown. She looks amazing naked. She even makes nude look stylish. That, to me, is a style icon. She could put a barrel on and it would be some sort of statement."
8. And Finally, Back to Hats
"If I'm wearing a trilby on the course, I'll wear it all day. I'm not wearing it because I think it looks good on the golf course; I'm wearing it because I woke up that morning and I said, 'I feel like wearing a fucking hat!' It's as simple as that for me."
A few days after golfing with Timberlake, I watched a clip of him at the charity event he attended the previous night (the one with the guy in the Rob Lowe fedora). On the course, Timberlake had recited, label for label, what he had thrown on before walking out the door that night—slim gray Dolce & Gabbana tux pants, a black William Rast V-neck T-shirt with a dog-tag necklace, and a pair of studded Martin Margiela dress shoes with pink-and-purple argyle socks: "Your sock game has gotta be right if you're gonna wear dress shoes," he explained. My first thought was: What the hell was he thinking? And then, when I saw the images, it all added up. He wore the tux pants loose and easy, instead of stiff and formal. The T-shirt hung untucked, hitting exactly at his belt line. Even the dog tag looked right. And, I guess, why shouldn't it have? The guy is the King of Pop—he can wear whatever the hell he wants.
1. Harless married Timberlake's mother, Lynn, when Justin was 5. An avid golfer, he taught Justin how to swing a golf club when he was 10 years old. For Harless's fiftieth-birthday-and-retirement present last year, Timberlake flew him in a private jet to Augusta National Golf Club for a day of golf at the home of the Masters.
2. Timberlake has stuck with his dad's example. When I meet him on the course, he's sporting a generous, fluid break on his black J.Lindeberg golf pants—same as he did on tour with the white three-piece-suits.
3. I first met Timberlake three years ago at a dinner to promote the launch of William Rast. There were about a dozen of us there—a handful of magazine editors; Timberlake himself; his mom (who, along with Paul, manages him); his cousin Rachel Yarbrough, who serves as his personal assistant; and his boyhood friend and partner in William Rast, Trace Ayala. After finishing our entrées, we abruptly hopped into a convoy of SUVs to Madison Square Garden, where Timberlake jumped onstage to perform a song with the Black Eyed Peas. Lynn then insisted on sticking around the sky suite to sing along with Fergie on "My Humps" before we hopped back into the SUVs to head to Bloomingdale's for an in-store appearance by Timberlake and Ayala. All of this, somehow, transpired promptly between the hours of 7 P.M. and 9 P.M.
4. Another thing you notice about Timberlake when you're on the course with him: the dude is piped these days. And there's a reason. This spring he'll climb Mount Kilimanjaro as part of a charity effort called Summit on the Summit, an initiative to raise awareness of the water shortage in Africa. "I've been training four times a week to get my VO2 levels up to expand my lungs. We'll climb for a week straight, carrying thirty pounds on our backs. It's going to be intense. But it's going to be so rewarding. Plus, we're going to be ready for it."
5. Close—Coco Chanel (founder of the label for whom Karl Lagerfeld now designs).