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21 Times Justin Timberlake Wore Some Very Cringeworthy Fashions

It was a long, long road to suit and tie.

1. The time he showed up to an awards show in a Missy Elliot Supa Dupa Fly-era ski suit.

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2. The time he and Lance Bass had an ugliest pants contest on the red carpet.

Jeff Kravitz / FilmMagic, Inc

Justin coordinating his coat to his pants FTW. (Really a loss though.)

3. The time he wore bedazzled leather.

Barry King / WireImage

4. The time he was dressed like a Fort Worth area pimp, circa 1977.

5. The time he wore this tie-dye silk and denim monstrosity — that he clearly got from the clearance rack of a Daffy’s.

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RIP Daffy’s.

6. The time he wore Britney’s sheer sparkle blouse and she was forced to wear just her slip.

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7. The time he wore the infamous denim suit…

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8. …which he then recycled it into this fugly jacket.

Ron Galella / Getty Images

Why didn’t someone stage a denim intervention?!

9. The time he was dressed like a mafia don going to church on Easter Sunday.

Ron Galella, Ltd. / WireImage

10. The time he dressed like Avril Lavigne.

James Devaney / WireImage

Oh Justin, you’re such a Sk8 Boi in your Hot Topic best!

11. The time he paid homage to Velma from Scooby-Doo.

Arnaldo Magnani/ Hulton Archive / Getty Images

Ugh and that bandana.

12. When he continued sporting bandanas, which was made worse, in this case, with a ringer tee from the Delia’s Catalog.

Chris Hondros/ Hulton Archive / Getty Images

13. The time he wore inkblot test pants.

KMazur / WireImage

I see a butterfly.

14. The time he wore these jeans with a skid mark on the crotch.

Edwine Seymour / Getty Images Entertainment

15. The time he wore this and didn’t realize he looked like the Kool-Aid Man.

Dave Benett / Getty Images Entertainment

“Oh, yeah!”

16. The time he wore a Von Dutch trucker hat; which he tilted sideways, of course.

James Devaney / WireImage

Sorry, but these NEVER looked good.

17. The time he wore a suit made from old carpet remnants from the Palms Casino, and topped it off with a clown tie.

Frank Micelotta/ Hulton Archive

Seriously, what the hell is going on with this suit? It’s like a Magic Eye poster.

18. The time he wore THESE pants:

Robert Mora / Getty Images

I guess he wanted the best of both worlds?

19. The time he accessorized his injured photo with sexy nurses.

SGranitz / WireImage

Yeah: Sexy nurses + bling + fedora = not douchie at all!

20. The time his ruffled leather shirt, studded bandana, and cornrows all competed for most heinous thing EVER!

Jeff Kravitz / FilmMagic, Inc

It’s really a toss-up.

21. The time he dressed like a second-rate 2Pac impersonator, and topped the look off with a pager strapped to his bandanna.

On second thought, he looks awesome and needs to bring back this look ASAP!

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