▲As the years passed, his taste started to become more refined. Here's a good example of a more sophisticated look.

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

▲Timberlake wearing Timberlands. A real denim bad boy!

▲A nice choice. John Travolta would be proud.

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

▲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.

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

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

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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.

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

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

▲JT arrives in style, after parking his spacecraft.

▲Timberlake was definitely in sync—with a disastrous fashion sense.

▲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?

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

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

▲We wonder if we'll ever see Justin Timberlake wearing cornrow braids again.

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

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

▲Justin Timberlake rocking the geek chic style.

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

▲Justin Timberlake looks absolutely handsome in this smart casual ensemble.

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

▲Timberlake looking trendy and cool with a stylish overcoat.

▲Justin Timberlake trying to pull the grunge-chic look.

▲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.

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

▲Justin always dreamed of dressing up like a winter sports coach. On this day, his dream came true.

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Justin Timberlake's style has evolved considerably throughout his career, and thank goodness for that! From the errors of his early teen pop star days to his transformation into a sophisticated gentleman on the red carpet, he's come a long way. In this gallery, we look back at the award-winning artist's style evolution, from his worst fashion faux pas moments to the times he brought sexy back. Check it out!