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. Via ztams.com 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. Via buzzworthy.mtv.com On second thought, he looks awesome and needs to bring back this look ASAP!