Initially it seemed fun and harmless. Those apple-cheeked boy bands practicing their cute choreography in silky, billowy ensembles that said “We’re romantic” or hip-hop-influenced uniforms that said “We’re tough, but not too tough for you, girl.” But the formula spread like mononucleosis to other groups. And as the millennium passed, it took boy-band graduate Justin Timberlake several years to shake the sartorial lessons of his ’N Sync salad days. His once-frosted curls grew out to soft brown before they were shorn altogether. The stage clothes hopefully found a home as dust rags where they could do no further harm. More than 15 years later, Timberlake is hardly recognizable. The scamp in the oversize jorts is now a suave star in a custom Tom Ford suit. Here’s a look at his bumpy fashion journey.
1. The formative years: The members of ’N Sync often dressed as if they had a clothing allowance to shop at the Gap when their debut album arrived in 1998. Early promotional photos were interchangeable with yearbook pictures of high school honor society students.
2. Boy-band megastardom: With the release of 2000’s “No Strings Attached,” the boys wanted to show that they were all grown up. They battled their former management team and broke free. But clearly they should have broken free of their costume designer. Timberlake appears to be wearing castoffs from a low-budget revival of “The Wiz.”
3. Cornrow scandal: His early hair experiments were as problematic as his wardrobe faux pas. Most offensive was his disturbing homage to Bo Derek. It’s too obvious, but we’ll say it anyway: This hairstyle is not a 10.
4. What a difference a year makes: At the 2001 MTV Video Music Awards, we begin to see a proto-solo Timberlake. The hair has been tamed, but the wardrobe looks like it was purchased at an airbrushing stand on a pier in a honky-tonk beach town.
5. Urban cowboy: Which was worse, the cornrows or his infamous Canadian tuxedo, which matched then-girlfriend Britney Spears’s denim evening gown? Definitely the denim.
6. All grown up: Free of bandmates, Britney, and troublesome hair, Timberlake found commercial and fashion success with the release of “Justified” in 2002. The do-rags and glitter of ’N Sync were discarded in favor of motorcycle jackets, jeans, and a reliance on his own talent.
7. Model behavior: After nearly a decade of dropping wardrobe bombs, Timberlake paired with friend Trace Ayala to create the clothing line William Rast. For several seasons, the brand showed at New York Fashion Week, but Timberlake’s attempt to revive acid-wash denim thankfully found little success.
8. Dressed for success: Timberlake’s formal side emerged with his 2006 album “FutureSex/LoveSounds.” But his stage ensemble was an ill-fitting attempt at playing dress-up. The only thing properly tailored to the singer’s lithe frame was the vest. Here’s hoping he returned the pants to Men’s Wearhouse at the conclusion of the tour.
9. Revenge of the nerd: The glasses may scream “Please take me seriously as an actor,” but as he neared 30, the superstar showed all nerds that he was sexier than they could ever hope to be in this retro getup.
10. Suit and tie: In a word, stunning. The unruly curls have been gelled and plastered into a leading man-worthy coiffure, and a collaboration with designer Tom Ford means the singer wears nothing but custom-made suits. This almost makes us forget the 2001 Canadian tuxedo... almost.