1. The time he wore this shirt that came straight from the clearance section of Delia’s Fall ‘99 catalog.
2. The time he was dressed in this Asian inspired outfit, which somehow was made even worse by the crushed velvet skirt (?).
3. The time he tried to pull off the look again.
4. The time we wore these cargo patchwork jeans.
I realize it was the late ’90s, but CARGO JEANS!
5. The time he wore one of Cruella de Vil’s old coats.
Also, was Chris Kirkpatrick in a Counting Crows cover band at some point?
6. The time he was dressed head to toe in acid wash at the AMAs.
But props on his Punky Brewster T-shirt.
7. The time he was forced to wear Missy Elliott’s Supa Dupa Fly-era hand me downs.
8. The time they dyed his hair the same shade as Ronald McDonald…
9. …and then color coordinated it with his shirt. Clearly, Britney was NOT impressed.
Also, those are some MAJOR cuffs on those jeans.
10. And when they again, color coordinated his hair to his outfit.
Also, LOL Justin’s necklace, it’s clearly from Chico’s.
11. The time he wore this frumpy lab coat/denim blazer combo.
12. The time he rocked a sleeveless leather jacket…
Even Jessica Simpson couldn’t keep a straight face.
13. …which was made even worse it was coordinated with purple python pleather pants.
Which is probably why he is trying to hide behind Lance and Justin.