Image via Complex Original
There's no one better to do a Complex Style History on than Justin Timberlake. He's been famous since childhood, which means there's been a camera on him at all times since 1992. There's photo evidence of his style which has progressed from his squeaky clean Mickey Mouse Club days to the frosted tips he rocked with 'N Sync to his current Tom Ford suit habit.
There's also no better time than now to look back at JT's fashion choices. He's on fire right now. His comeback performance at this year's Grammys showed that he hasn't lost the swag from his FutureSex/LoveSounds days. He's promoting his new album, 20/20 Experience, and doing a joint tour with Jay-Z. He'll be hosting SNL again on March 9, and will appear onLate Night With Jimmy Fallon for a whole week. So with all the good stuff going on in his life, a little teasing at his past outfits can't hurt too bad, right? The Memphis boy has had a wild sartorial ride from 1992 until now. See it all in Style History: Justin Timberlake.
Mikey Mouse 1
Where: Mikey Mouse Club
When: 1992
Complex Says: Wearing a cap backwards is never not cool, but it was at its peak in '92.
Mikey Mouse 2
Where: Mikey Mouse Club
When: 1992
Complex Says: All over print shirts are back, and Justin's print from '92 is exactly what cool kids are looking to wear right now.
Mikey Mouse 3
Where: Mikey Mouse Club
When: 1992
Complex Says: First of all, notice how they forgot an arrow pointing to Ryan Gosling (on Justin's left). Second, this is the epitome of kids' styles in the early '90s. The striped shirts, oversized fits, and vests! Also note JT's awesome haircut. Tell us you didn't have that when you were in 5th grade.
Beauty Pageant
Where: Beauty Pageant in Tennessee
When: 1993
Complex Says: In another world, Justin would've been a magician.
Mickey Mouse 4
Where: Mickey Mouse Club
When: 1993-1994
Complex Says: Does JT look like a young George Michael Bluth? (Also, looks like Brit Brit was the brains behind that matching denim number seven years later.)
Billboard Awards
Where: Billboard Awards
When: December 7, 1998
Complex Says: Holy shit, it's like the Beatles took a time machine to the '70s, took the disco era's worst possible drugs, and catapulted into '98 looking HORRENDOUS. Let's just take a minute to soak in Justin's paisley carpet pants (are they shiny?) and XXXXL shirt cuffs. And bleached curls. And black undershirt. And baby chain.
Unknown 1
Where: Bop Magazine
When: Unknown
Complex Says: Yikes. Let's start with the good news: Tommy Hilfiger gear was cool, and now that it's "vintage," it's still pretty cool. The bad news: Hoop earrings! AND a cartilage stud! And taking style tips from wet golden retrievers.
Teen People Anniversary
Where: Teen People's First Anniversary Party
When: January 6, 1999
Complex Says: This might look wack now, but it was absolutely on trend and on point in '99. Carpenter jeans and a Tommy Hil windbreaker? Swaggin'.
26 American Music Awards
Where: 26th Annual American Music Awards
When: January 11, 1999
Complex Says: Oh, y'all ain't know? 'N Sync was the first boy band to go to space!
Unknown 2
Where: Unknown
When: Unknown
Complex Says: Chain game extra smedium. Bleach game extra strong.
Unknown 4
Where: Bop Magazine
When: Unknown
Complex Says: Even with style like this, Mr. Timberlake was the original teen heartthrob named Justin. Bow down, Biebs.
MTV Video Music Awards 1
Where: MTV Video Music Awards
When: September 7, 2000
Complex Says: Justin Timberlake was a part of Lonely Island before Lonely Island was Lonely Island. The combo of the knit turtleneck, the so-bad-it's-on-purpose hair, and diamond earrings just scream "SNL Digital Short."
Wango Tango Concert
Where: Wango Tango Concert
When: May 13, 2000
Complex Says: Every famous white man with semi-long hair has experimented with corn rows. They just can't say no. Luckily, Justin was in this phase early and most of the world has forgotten about it. Until now.
Unknown 3
Where: Unknown
When: Unknown
Complex Says: Justin went a step further with his frosted tips and added some red Manic Panic to that shit. Bong. We can't hate on the jersey and mini chain style, though, because it's what we all wore in 2001.
Coyote Ugly
Where: Coyote Ugly Movie Premiere
When: July 31, 2000
Complex Says: Justin was a pimp in training, so what better place to practice your game than at the Coyote Ugly premiere? He certainly tried his hardestEMDASH leather jacket, satin shirt, diamond earring, S-curl...
Unknown 5
Where: Unknown
When: Unknown
Complex Says: Fact: A$AP Rocky would rock the same outfit (but perhaps in Lance's colorway) right now.
27 People's Choice Awards
Where: 27th Annual People's Choice Awards
When: January 7, 2001
Complex Says: Justin and his four other boy band members moonlighted as pick-up artists back in the day.
28 American Music Awards
Where: 28th Annual American Music Awards
When: January 8, 2001
Complex Says: The infamous. Official red carpet murderers. Lesson learned: the couple who match Texas Tuxedos together, don't stay together.
SuperBowl 1
Where: Super Bowl XXXV
When: January 28, 2001
Complex Says: Justin's jacket looks like something Big Sean would wear today. A colorblocked leather with python detail on the side? RSVP Gallery is buying 10 of those right now. But who cares what JT's wearing, you should be busy looking at Britney's perfect abs.
43 Grammy Awards
Where: 43rd Annual Grammy Awards
When: February 21, 2001
Complex Says: Topcoat game strong. The ironic part is that you'd see similar offerings today from designers like Dries Van Noten. Who knew J Timbo and company were actually ahead of their time?
MTV Video Music Awards 2
Where: MTV Video Music Awards
When: September 6, 2001
Complex Says: We know how stylish Justin gets in less than a year after this, but man...it must suck to be wearing the craziest outfit the one time you're photographed with the King of Pop.
Unknown 6
Where: Unknown
When: Unknown
Complex Says: Avast! This pirate's outfit belongs in Davy Jones' Locker...
Superbowl 2
Where: Superbowl XXXVIII
When: February 1, 2004
Complex Says: Out of all the ridiculous outfits JT's worn over the years, we have to say that this here is the biggest style fail. You perform at the Super Bowl, let alone with Miss Jackson, and you wear that? Mark Zuckerberg tries harder.
46 Grammy Awards
Where: 46th Annual Grammy Awards
When: February 8, 2004
Complex Says: An early suit-and-tie sighting. It's slightly nerdy, but things are looking up.
Shag Nightclub
Where: Leaving Shag Nightclub
When: May 29, 2006
Complex Says: In 2006, Ashton Kutcher and JT's outfits were pretty much interchangeable.
Good Morning America
Where: Good Morning America
When: September 15, 2006
Complex Says: This is when the JT as we know him today started to emerge. His style during the FutureSex/LoveSounds era were all suits.
JT Last Live Tour
Where: JT Last Live Tour- The Future Sex/Love Show
When: February 7, 2007
Complex Says: The white suit was a style risk, so props regardless, but to pair it with white shell toes wasn't the right idea.
Hot Butter Club
Where: Leaving the Super Hot Butter Club
When: February 4, 2008
Complex Says: Straight out of the lookbook of his clothing line, William Rast, JT rocks the Euro look with a moto jacket, spring scarf, and washed denim.
Roseland Ballroom
Where: Roseland Ballroom
When: May 1, 2008
Complex Says: Justin was fully repping William Rast jeans on stage with Madonna.
51 Grammy Awards
Where: 51st Annual Grammy Awards
When: February 8, 2009
Complex Says: The patterned tux jacket is subtle because it's black on black with different textures. Totally appropriate for the Grammys.
William Rast Fashion Show
Where: William Rast Fashion Show
When: July 2, 2009
Complex Says: Did Trace Ayala dress Justin or did Justin dress Trace?
61 Emmy Awards
Where: 61st Annual Emmy Awards
When: September 20, 2009
Complex Says: Perfect tux game with the clean white pocket square. The thick black frames were spot-on in '09, too.
Tribeca
Where: Tribeca
When: July 9, 2010
Complex Says: Hard to judge style when it comes to workout gear, but the bandanna is a nice touch. Word to Frank Ocean.
US Open
Where: US Open
When: September 12, 2011
Complex Says: JT's rocking the perfect US Open fit. The chambray goes nicely with green chinos and for some rare reason, he doesn't look like a douche in a newsboy cap.
Costume Institute Benefit Gala
Where: Costume Institute Benefit Gala
When: May 7, 2012
Complex Says: Justin killed it here. Not only is his classic tux tailored perfectly, his date is a total babe, too.
Beverly Hills
Where: Beverly Hills
When: June 1, 2012
Complex Says: This look is so L.A., so we're not shocked he was in the 90210 when he wore this. A dark graphic tee with black jeans, low profile sneakers and shades is practically a uniform.
Union Square
Where: Union Square, New York City
When: November 11, 2012
Complex Says: The harrington jacket with the large check shirt and short brimmed hat gives him a cool British Mod flair.
NYC
Where: New York City
When: December 4, 2012
Complex Says: Droopy beanies are never the right move, but the coat is cool with an interesting silhouette.
20 SAG Awards
Where: 20th Annual SAG Awards
When: January 27, 2013
Complex Says: Fashion critics didn't like this Tom Ford suit—they thought it was too playful for the black-tie SAG Awards. But we think it was cool for JT to switch it up as a musician at an actor's ceremony.
55 Grammy Awards 1
Where: 55th Grammy Awards
When: February 10, 2013
Complex Says: The guitar reminds us that Justin is from Memphis afterall, and the sharp haircut looks like something one of these barbershops cooked up.
55 Grammy Awards 2
Where: 55th Annual Grammy Awards
When: February 10, 2013
Complex Says: This preview of what one could see at the "Legends of the Summer" Tour was pretty epic and stylish. Two musical greats in Bond-like tuxedos.
55 Grammy Awards 3
Where: 55th Annual Grammy Awards
When: February 10, 2013
Complex Says: Justin killed it in his comeback performance at this year's Grammys. He made a classic tuxedo far from boring with a pocket square with contrasting trim, and black-and-white loafers.
Tom Ford Fashion Show
Where: Tom Ford fashion show, London fashion week
When: February 18, 2013
Complex Says: Of course the unofficial Tom Ford ambassador would be at the designer's fashion show. Justin Timberlake kills it again and his suit-and-tie game is definitely the one to beat this year.
