It’s been five long years since Justin Timberlake released his last album, FutureSex/Love Sounds. And with this Friday’s premiere of In Time marking J.T.’s fifth — yes, fifth, as in, four more than Kate Winslet — movie in the past twelve months, we’re guessing our workout playlists aren’t getting freshly Timberlaked anytime soon. (Will no one think of the cardio?) Indeed, Timberlake has come a long way since his late-nineties rise to fame, from boy band heartthrob to legit musical force, to Saturday Night Live comedy star, to now, where he appears to want “actor” to be the first word in his hyphenate. Clearly, it’s time for a slideshow examining how his style has morphed along with his résumé; the answer is “considerably,” because when your starting point is wearing head-to-toe matching denim with your girlfriend, there is nowhere to go but up.
Why: The WB Radio Music Awards, a.k.a., something we’re pretty sure doesn’t exist anymore
What: It’s hard not to be distracted by JC Chasez’s turtleneck — he looks like he was styled by Ellen DeGeneres — but once you tear your eyes away from him, why, there’s Justin Timberlake, sporting a velvet overcoat and a necklace made from something unearthed from an Indian burial ground. Why didn’t we realize the nineties were so weird when we were living through them?
Photo: Brenda Chase
Why: The always fun-to-say Wango Tango concert
What: Justin’s cornrows — not to mention his Dazed and Confused–inspired glasses — are transfixingly terrible, kicking off a long and often painful series of attempts to revolutionize his own head. Clearly The Lou Pearlman Guide to Being in a Boy Band didn’t have a chapter called “Leaving Well Enough Alone.”
Photo: Getty Images/2000 Getty Images
Why: Good question
What: Oh, JUSTIN. The do-rag, the patchy shirt, the leather pants that look like they’re adorned with boy band merit badges for achievement in pelvic thrusting and close-harmony singing … It’s like he’s the honcho of the wussiest biker gang in Hollywood. Actually, in some senses, it’s possible he was.
Photo: Getty Images
Why: The Teen Choice Awards, and an album launch party for his then-girlfriend Britney Spears (sniffle)
What: For Justin, apparently Teen Stardom requires leather. But these aren’t, like, hard-core rock-and-roll leather; they’re leather for someone who wants people to think he’s rock and roll, but who actually prefers choreographed dance numbers and talking about his and his girlfriend’s possibly fictional virginity. Which … hey, whatever works for you, dude, as long as you stop by a tailor first.
Photo: Chris Weeks
Why: American Music Awards
What: Ten years after the fact, Justin and Britney’s His ‘n’ Hers matching denim formalwear is still so astoundingly awful, so jaw-droppingly, hilariously terrible that it makes us nostalgic for the Time Before Stylists. Everything was so funny then — especially the idea that you and your famous girlfriend should attend a major awards show dressed as the king and queen of the Pig Wrasslers’ Annual Prom and Tractor Roadshow.
Photo: LUCY NICHOLSON
Why: Lennox Lewis and Mike Tyson’s WBC/IBF Heavyweight Championship fight
What: We’re beginning to think Justin flat-out hated his trademark curly locks. This hat, which makes him look like he’s running late for his shift selling incense on the Venice boardwalk, can only possibly be excused by assuming he was grieving his breakup with Britney (as, of course, were we all). In his position, a woman would have cut some ill-advised bangs; perhaps a goofy knit skullcap is Justin’s bangs-equivalent, without that messy growing-out period.
Photo: Robert Mora/2002 Getty Images
Why: VMAs and Teen Choice Awards
What: We’re beginning to think Justin’s relationship with his head — and whatever’s growing on top of it — is something that requires professional intervention. Here, yhe Inaugural Year of the Fedora (a look Justin still revisits occasionally) only serves to confirm our suspicion that he can only live with his hair by stuffing it into something. The furry one even looks like some kind of hair-replacement experiment. That piece of psychoanalysis is free, Justin, but next time we charge by the hour. P.S.: Your hair is fine.
Photo: Dave Hogan/2002 Getty Images
Why: Performances on the Justified tour, and at the Brit Awards
What: Justified, Timberlake’s first solo album, had much to tell us: It called out Britney Spears for (allegedly) cheating; it implored us all to rock our bodies; and, apparently, it was a lengthy and subtle endorsement of the white tracksuit as a fashion choice. We’re sure he was trying to break away from boy-band lunacy by cleaving to something he thought was cooler, but we think he should’ve stopped short of robbing Gwen Stefani’s closet.
Photo: Dave Hogan/2003 Getty Images
Why: The VMAs
What: Next to the cornrows, the tracksuits, and the mad hattery, this suit is practically plucked from Cary Grant’s wardrobe — although, if we’re being picky, and of course we are, it actually looks a bit off-the-rack. And unfortunately, JT bowed to conventional VMA wisdom and paired it with clunky, obvious kicks. They may be easier to dance in, but there’s a reason people change between the red carpet and the stage, dude.
Photo: Frank Micelotta/2003 Getty Images
Why: The Grammy Awards
What: “What do we think? Do you buy me MORE or LESS as a serious multiple Grammy winner if my shirt is the color of the fish course?” Our answer: This is a step in the correct, more sophisticated direction, but there’s a reason Justin was still a few years away from bringing sexy back.
Photo: Frederick M. Brown/2004 Getty Images
Why: The VMAs again
What: JT is a changed man from the one who hit the red carpet of the 2003 VMAs sporting giant, goofy sneaks. The commitment to improvement is admirable, but his commitment to fit is questionable — this makes him look like someone’s cigar-smoking elderly dad, exactly not the person we want to picture in conjunction with the words FutureSex/LoveSounds.
Photo: Evan Agostini/2006 Getty Images
Why: The debut showing of Timberlake’s clothing line, William Rast
What: This is when Timberlake’s style truly starts to turn, which makes sense, given that it’s also when he started selling clothes and therefore needing to entice people to buy them. It’s a very good look: The jeans that are the brand’s specialty fit well (finally!), and the whole aura is, if not quite “hot professor,” definitely “the adorable T.A. who is endearingly too busy reading Important Authors to shave his neck.”
Photo: Michael Buckner/2006 Getty Images
Why: The premiere of Alpha Dog, Justin’s first big acting role (unless you count his stint alongside Kathie Lee Gifford in the TV movie Model Behavior
, which of course we do)
What: Justin seems to be under the impression that actors dress more nerdily than musicians do. He may be right. This outfit is crisp, but imagine it with jeans — which he ought to be wearing as the figurehead of a denim line, anyway — and it feels a bit more indie and relaxed, rather than achingly hipster. And somehow Justin still doesn’t seem to know which shoes to pair with what. We’d love to help, but we’re generally pondering the exact same question in front of our own closets. Stars: They’re just like us.
Photo: Vince Bucci/2007 Getty Images
Why: Shrek the Third promotional events, at which he had to make nice with his ex-girlfriend Cameron Diaz
What: This must have been Justin’s Harmless Chic phase (in fairness, after releasing “SexyBack” in 2006, it would’ve been awfully literal of him to run around town in a codpiece and chaps). Everything Timberlake wears here is classy and cool, but also calculatedly and decidedly nonthreatening. He could be your math tutor, or attend your church socials, or run your bowling league. When you’re the voice in a kids’ movie, that seems both an apt, and a mature, savvy decision to marry his style to the product he’s selling at the moment.
Photo: Frederick M. Brown/2007 Getty Images
Why: Hosting American society’s proudest awards celebration, the ESPYs
What: JT cemented his status as Not Just Another Mezza Soprano when he hosted sports’ sixteenth most important night — and in a custom monogrammed tracksuit, no less. In case you’re wondering, “successfully hosting an awards show in a custom, monogrammed tracksuit” is No. 6 on a list titled Six Ways You Know You’re Famous Enough to Get Away With Pretty Much Anything.
Photo: Kevin Winter/2008 Getty Images
Why: Fashion Rocks
What: Can’t you just hear the wheels turning? “Fashion rocks. Okay. So. Fashion, and rock. So that means … rock on the bottom, fashion on the top, right? Right? Hello? Anyone? What am I supposed to do with these jeans?” Unless this was during some great tailoring strike of 2008 that history tragically forgot, we suggest scissors. Can’t look any worse.
Photo: Stephen Lovekin/2008 Getty Images
Why: Keep a Child Alive charity gala
What: JT, in fairness, is really starting to pull it all together, but that blasted fedora is back. It gives the impression that Justin is not so much interested in raising money as he is in making this quick because he’s in a very big hurry to do some surveillance at a nearby swing-dance-athon.
Photo: Rob Loud/2008 Getty Images
Why: the SAG Awards
What: With Justin’s music a distant memory, nothing says, “I am a REAL ACTOR,” like wearing a tux at an awards show devoted solely to actors. And nothing says, “Tee hee, except remember that time Britney and I wore matching denim outfits?” like a pleated chambray dress shirt. Dude, we hate to break it to you, but you’re supposed to be trying to make us forget that.
Photo: Frazer Harrison/2010 Getty Images
Why: Promotion of The Social Network
What: Glasses! Lots of ‘em. We’re not saying they’re fake; merely that it’s deeply hilarious how religiously Justin broke them out with his poshest suits at every single event for this Oscar contender. (Seriously, there were at least six or seven other photos we were tempted to show you.) Perhaps he utilized them so rigorously with the goal that they would underline and highlight and then circle the statement that he is Serious and Important and Sorkinesque.
Photo: Andrew H. Walker/2010 Getty Images
Why: The premiere of his crowning achievement, Yogi Bear
What: Remember those brainy fancy-movie specs? Gone, in favor of face-blocking aviators. So telling.
Photo: Jason Merritt/2010 Getty Images
Why: The Bad Teacher premiere
What: Luckily, Justin’s outfit isn’t as bad as the teacher (nor the movie). Sometimes, it’s nice to step back and enjoy a moment of simplicity, with just the two bars on the jacket’s lapel giving this its flair. Very sleek, fitted, smooth … a sartorial palate-cleanser, the sorbet of suits: works between meals, but can be a nice course on its own too.
Photo: Stephen Lovekin/2011 Getty Images
Why: Friends With Benefits premiere
What: J.T. still appears to be taking this acting racket seriously. (Why? Why? Make a new album, Justin.) This is his first turn as a romantic lead in a movie, and with this open-shirted, light-colored leisure suit look, he appears to be taking a page from the man playing the romantic lead in (seemingly) every other movie: Ryan Gosling. Do we smell a man-crush? Well, everyone else has one, why not JT?
Photo: Stephen Lovekin/2011 Getty Images
Why: In Time premiere
What: We’ve gone from “Ryan Gosling lite” to “recently spent several days perusing every Ryan Gosling–themed Tumblr.” We get the instinct — Gosling is the mainstream and indie actor of the moment, and yet maintains his own distinct personal style — but we also think we’ve seen this particular movie, and it was called Single White Female, and it ended badly, and everyone had red hair. None of that sounds like a solid career move for either of these gents at this point, but we’ll give this much to Justin: Like Gosling, he’s gotten us curious about where he’ll go next, and more important, what he’ll be wearing when he gets there.
Photo: Frazer Harrison/2011 Getty Images