25. Mighty Healthy "Mad People in New York are Hustlers"

Released: 2005

T-shirts with messages are, for the most part, pretty lame. If you feel the need to walk around with some self-important proclamation on your chest, you should probably just get on Twitter ASAP. But this tee using magazine names and their typography is one of the most original, both in message and treatment.

The guys behind Mighty Healthy don't just comment on the culture through their clothes, they also participate. Hit up their site for an awesome pirate radio station.