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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.

    SGranitz / WireImage

    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.

    Christina Radish/ Redferns

    RIP Daffy's.

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

    Jim Smeal/ Ron Galella Collection / Getty Images

    7. The time he wore the infamous denim suit...

    KMazur / WireImage

    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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