22. In4mation "Katie"

Released: 2006

For obvious reasons (namely the U.K.'s insane libel laws), this tee most certainly does not feature an image of one Kate "Katie" Moss. In fact, any resemblance is purely coincidental, and likely a result of your own out-of-control cocaine and rice cake habit.

YOU AUGHTA KNOW:
In4mation did another T-shirt that definitely did not feature a slightly altered image of supermodel Cindy Crawford.