1. The time he showed up to an awards show in a Missy Elliot Supa Dupa Fly-era ski suit.
2. The time he and Lance Bass had an ugliest pants contest on the red carpet.
Justin coordinating his coat to his pants FTW. (Really a loss though.)
3. The time he wore bedazzled leather.
5. The time he wore this tie-dye silk and denim monstrosity — that he clearly got from the clearance rack of a Daffy’s.
6. The time he wore Britney’s sheer sparkle blouse and she was forced to wear just her slip.
7. The time he wore the infamous denim suit…
8. …which he then recycled it into this fugly jacket.
Why didn’t someone stage a denim intervention?!
9. The time he was dressed like a mafia don going to church on Easter Sunday.
10. The time he dressed like Avril Lavigne.
Oh Justin, you’re such a Sk8 Boi in your Hot Topic best!
11. The time he paid homage to Velma from Scooby-Doo.
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.
13. The time he wore inkblot test pants.
I see a butterfly.
14. The time he wore these jeans with a skid mark on the crotch.
15. The time he wore this and didn’t realize he looked like the Kool-Aid Man.
16. The time he wore a Von Dutch trucker hat; which he tilted sideways, of course.
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.
Seriously, what the hell is going on with this suit? It’s like a Magic Eye poster.
18. The time he wore THESE pants:
I guess he wanted the best of both worlds?
19. The time he accessorized his injured photo with sexy nurses.
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!
It’s really a toss-up.