#13 Carlito: Do You Spit or Swallow?
Carlito was pretty vastly underrated during his tenure in WWE. He was a compelling and often funny heel that spat apple chunks in the face of people who "didn't want to be cool".
So of course, WWE just had to make a sexual pun out of it (psst, by the way - that's a hint for a lot of the rest of the list).
I get that the Carlito character wasn't really supposed to be taken all that seriously, but this shirt was a grave injustice. While not aesthetically awful, it drew little to no connection to the character it was assigned to. Carlito wasn't a sexual deviant - he was just a cool guy that liked apples.
Plus, did they honestly expect anyone to step outside wearing this shirt? Good luck finding a place that would even allow you to. And imagine if someone tried to wear this shirt out somewhere in 2017...yikes.