See Also
See Again
© Shutterstock
0 / 29 Fotos
Braids and shades - We wonder if we'll ever see Justin Timberlake wearing cornrow braids again.
© Getty Images
1 / 29 Fotos
NSYNC - What was it with the extra-long sleeves? Didn't NSYNC have a tailor back then?
© Getty Images
2 / 29 Fotos
NSYNC - The '90s were indeed a dark period in Justin Timberlake's style. But at least he wasn't alone.
© Getty Images
3 / 29 Fotos
Overcoat fail - Timberlake was definitely in sync—with a disastrous fashion sense.
© Getty Images
4 / 29 Fotos
Suit - Believe it or not, three-button striped suits used to be fashionable.
© Getty Images
5 / 29 Fotos
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?
© Getty Images
6 / 29 Fotos
Arr! - Look everyone, I'm a pirate wearing an outfit made by a five-year-old!
© Getty Images
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Shirt - Justin Timberlake and Britney Spears back in 2002. Who needs an ironed dress shirt anyway?
© Getty Images
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Space oddity - JT arrives in style, after parking his spacecraft.
© Getty Images
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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.
© Getty Images
10 / 29 Fotos
Got denim? - Timberlake wearing Timberlands. A real denim bad boy!
© Getty Images
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Mixing styles - When you go play polo but don't want to lose your street cred.
© Getty Images
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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.
© Getty Images
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Saturday Night Fever - A nice choice. John Travolta would be proud.
© Getty Images
14 / 29 Fotos
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.
© Getty Images
15 / 29 Fotos
Super cuffs - 'Spider-Man' had just hit the theaters, so maybe he was secretly hoping those leather cuffs would give him superpowers.
© Getty Images
16 / 29 Fotos
It's cold in here - Justin always dreamed of dressing up like a winter sports coach. On this day, his dream came true.
© Getty Images
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Casual cool - Justin Timberlake trying to pull the grunge-chic look.
© Getty Images
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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.
© Getty Images
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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.
© Getty Images
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Elegance - Cartier was celebrating its 100th anniversary in America, and Timberlake dressed up for the occasion. Classy!
© Getty Images
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Smart casual - The pocket handkerchief gives his smart casual outfit a nice touch.
© Getty Images
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Glasses - Justin Timberlake rocking the geek chic style.
© Getty Images
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Pattern mix - Who would have thought a skull-print skinny tie would look great with a striped shirt?
© Getty Images
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Hip - Timberlake looking trendy and cool with a stylish overcoat.
© Getty Images
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Gentleman - Justin Timberlake looks absolutely handsome in this smart casual ensemble.
© Getty Images
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Classy - Timberlake dazzling on the red carpet, wearing a classy tux.
© Getty Images
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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
© Getty Images
28 / 29 Fotos
© Shutterstock
0 / 29 Fotos
Braids and shades - We wonder if we'll ever see Justin Timberlake wearing cornrow braids again.
© Getty Images
1 / 29 Fotos
NSYNC - What was it with the extra-long sleeves? Didn't NSYNC have a tailor back then?
© Getty Images
2 / 29 Fotos
NSYNC - The '90s were indeed a dark period in Justin Timberlake's style. But at least he wasn't alone.
© Getty Images
3 / 29 Fotos
Overcoat fail - Timberlake was definitely in sync—with a disastrous fashion sense.
© Getty Images
4 / 29 Fotos
Suit - Believe it or not, three-button striped suits used to be fashionable.
© Getty Images
5 / 29 Fotos
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?
© Getty Images
6 / 29 Fotos
Arr! - Look everyone, I'm a pirate wearing an outfit made by a five-year-old!
© Getty Images
7 / 29 Fotos
Shirt - Justin Timberlake and Britney Spears back in 2002. Who needs an ironed dress shirt anyway?
© Getty Images
8 / 29 Fotos
Space oddity - JT arrives in style, after parking his spacecraft.
© Getty Images
9 / 29 Fotos
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.
© Getty Images
10 / 29 Fotos
Got denim? - Timberlake wearing Timberlands. A real denim bad boy!
© Getty Images
11 / 29 Fotos
Mixing styles - When you go play polo but don't want to lose your street cred.
© Getty Images
12 / 29 Fotos
What? - It's all a bit of a mess. We feel like crying a river when we look at those accessories.
© Getty Images
13 / 29 Fotos
Saturday Night Fever - A nice choice. John Travolta would be proud.
© Getty Images
14 / 29 Fotos
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.
© Getty Images
15 / 29 Fotos
Super cuffs - 'Spider-Man' had just hit the theaters, so maybe he was secretly hoping those leather cuffs would give him superpowers.
© Getty Images
16 / 29 Fotos
It's cold in here - Justin always dreamed of dressing up like a winter sports coach. On this day, his dream came true.
© Getty Images
17 / 29 Fotos
Casual cool - Justin Timberlake trying to pull the grunge-chic look.
© Getty Images
18 / 29 Fotos
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.
© Getty Images
19 / 29 Fotos
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.
© Getty Images
20 / 29 Fotos
Elegance - Cartier was celebrating its 100th anniversary in America, and Timberlake dressed up for the occasion. Classy!
© Getty Images
21 / 29 Fotos
Smart casual - The pocket handkerchief gives his smart casual outfit a nice touch.
© Getty Images
22 / 29 Fotos
Glasses - Justin Timberlake rocking the geek chic style.
© Getty Images
23 / 29 Fotos
Pattern mix - Who would have thought a skull-print skinny tie would look great with a striped shirt?
© Getty Images
24 / 29 Fotos
Hip - Timberlake looking trendy and cool with a stylish overcoat.
© Getty Images
25 / 29 Fotos
Gentleman - Justin Timberlake looks absolutely handsome in this smart casual ensemble.
© Getty Images
26 / 29 Fotos
Classy - Timberlake dazzling on the red carpet, wearing a classy tux.
© Getty Images
27 / 29 Fotos
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
© Getty Images
28 / 29 Fotos
The evolution of Justin Timberlake's style
The entertainer turns 42 this January 31
© Getty Images
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!
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