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Braids and shades - We wonder if we'll ever see Justin Timberlake wearing cornrow braids again.

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NSYNC - What was it with the extra-long sleeves? Didn't NSYNC have a tailor back then?

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NSYNC - The '90s were indeed a dark period in Justin Timberlake's style. But at least he wasn't alone.

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Overcoat fail - Timberlake was definitely in sync—with a disastrous fashion sense.

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Suit - Believe it or not, three-button striped suits used to be fashionable.

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Facial hair - Goatees were a thing back then, but did anyone tell Justin Timberlake that he needed to actually have facial hair in order to grow one?

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Arr! - Look everyone, I'm a pirate wearing an outfit made by a five-year-old!

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Shirt - Justin Timberlake and Britney Spears back in 2002. Who needs an ironed dress shirt anyway?

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Space oddity - JT arrives in style, after parking his spacecraft.

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Fail -

Rocking a leather jacket paired with frosted tips, it's safe to say this is one of Timberlake's faux pas moments. Spears isn't exactly helping the ensemble either.

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Got denim? - Timberlake wearing Timberlands. A real denim bad boy!

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Mixing styles - When you go play polo but don't want to lose your street cred.

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What? - It's all a bit of a mess. We feel like crying a river when we look at those accessories. 

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Saturday Night Fever - A nice choice. John Travolta would be proud.

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New hairstyle - Years later, Timberlake was finally able to grow a goatee. Extra points for the haircut that turned him into one of the hottest bad boys in pop music.

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Super cuffs - 'Spider-Man' had just hit the theaters, so maybe he was secretly hoping those leather cuffs would give him superpowers.

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It's cold in here - Justin always dreamed of dressing up like a winter sports coach. On this day, his dream came true.

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Casual cool - Justin Timberlake trying to pull the grunge-chic look.

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Suit & tie - Justin Timberlake got it right this time. It does look like he's going for a job interview, but at least the suit is well-tailored.

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He's bringing sexy back - As the years passed, his taste started to become more refined. Here's a good example of a more sophisticated look.

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Elegance - Cartier was celebrating its 100th anniversary in America, and Timberlake dressed up for the occasion. Classy!

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Smart casual - The pocket handkerchief gives his smart casual outfit a nice touch. 

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Glasses - Justin Timberlake rocking the geek chic style.

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Pattern mix - Who would have thought a skull-print skinny tie would look great with a striped shirt?

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Hip - Timberlake looking trendy and cool with a stylish overcoat. 

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Gentleman - Justin Timberlake looks absolutely handsome in this smart casual ensemble.

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Classy - Timberlake dazzling on the red carpet, wearing a classy tux.

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Heartthrob -

Despite his more mature fashion sense,  Timberlake can still pull off a floral print bomber jacket like a true star.

See also: The 30 best boy bands of all time

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