The Style Evolution of Justin Timberlake

Categories Fashion

One of the world’s most stylish men turns 36 today . . . but he wasn’t always so fashion forward. To celebrate his birthday, we look back on the style path of “JT”.

Two-Minute Noodles — 2000

In an era when it looked like Timberlake and his N*Sync bandmates dressed themselves by rummaging through a rapper’s wardrobe blindfolded and emerging with whatever they could get their hands on, JT’s hair managed to overshadow some truly dodgy outfits . . . and we’re talking bedazzled bandanas, baggy acid-washed jeans, and graffiti-printed tank tops. Who could forget those tight bleached blond curls that look like he’d spilled a bowl of noodles on his noggin, or those short-lived corn rows.


Canadian Tuxedo — 2001

You know how people at Alcoholics Anonymous meetings talk about hitting rock bottom? Well, in style terms, that moment came for JT at the American Music Awards in January 2001, when he rocked up wearing a stone-washed, bell-bottom tuxedo with a matching cowboy hat, plus Britney Spears on his arm carrying a denim purse. Yikes.


Sexy Back — 2006

Justin experimented with a more mature look — including facial hair and a buzz cut — after he released his debut album Justified in 2002, but there were plenty more sartorial nightmares to come. After years of man jewellery, trucker caps, graphic tees, velour tracksuits, camouflage cargo pants, wardrobe malfunctions at Super Bowls, and fedoras (so many fedoras), Timberlake finally stumbled upon a look that worked in 2006 when he released his second album FutureSex/LoveSounds, modelled here at the 2006 VMAs in New York (if you can forgive the baggy suit pants).


Suiting Up — 2009

Hollywood must have made a positive impact on Timberlake’s wardrobe because his style game blossomed around the time he took a break from music to focus on his acting career, appearing in The Social Network, Friends with Benefits, and The Love Guru (yeah, we’d scrubbed that one from our memories, too). This perfectly tailored grey three-piece suit he rocked at Cartier’s 100th anniversary party in April 2009 started to erase the memories of that Canadian tux at the start of the decade.


20/20 Vision — 2014

Today, Timberlake is the definition of suave — thanks in no small part to his bromance with American designer Tom Ford, who produced 600 individual garments for JT’s 20/20 Experience World Tour. Ford has styled Timberlake on red carpets since 2011, as well as his glamorous Italian wedding to actress Jessica Biel in 2012, and his immaculate tuxedos for the 2014 tour consolidated JT’s status as one of the most fashionable celebrities on the planet.