27. WCW Four Horsemen
While the Horsemen are without a doubt the most legendary stable of the 1980s, they never really had a shirt that symbolized their dominance. It wasn't until the 1990s that WCW created a Horseman shirt that was sold for any extended period of time. The shirt wasn't as good as it could have been but the image was still pretty cool and hey, it's the Four Horsemen.
26. I'm Your Papi
A storyline that was so stupid it could only be saved by Eddie Guerrero, Latino Heat revealed that he was the real father of Rey Mysterio's son. It was completely ridiculous and completely over-the-top, so of course Eddie ran with it and turned into a cartoon super villain. Eddie revealed his fatherhood with a comically evil "I'm your papi!" statement on Smackdown and instantly created a very cool t-shirt.
25. Yes! Yes! Yes!
Released during Daniel Bryan's rise to popularity, the Yes Movement was still on it's climb when this Yes! shirt hit the market. Like many great shirts, the simpler the design, the better the shirt ends up being. This shirt summarizes Daniel Bryan quite nicely with his catchphrase and a wrestling ring.
24. Funk U
Terry Funk was hardcore before being hardcore was cool and he also had one of the best t-shirts for years. The Funk U shirt dubbed Terry as the professor of hardcore and really, who else would you rather have? Obviously, this was a play on words but who was going to tell the Funker he couldn't wear his t-shirt?