It's hard to wear a political tee without looking like a jerk: if you really believed in "Change", wouldn't you have put on a fresh shirt by now? For something truly different, check out e.5.charlie.
While they've got a range of prints on their 100% cotton baby-soft jersey-knit tees, Hub-based streetwear outfit e5c's newest drop's lifeblood is political garb you'd actually wear, perfect for the dude who joined Model UN strictly to get closer to some sweet Azerbaijina. Poli-designs include a derisive "Black House" number w/ a film-negative-style picture of the White House, the red "Bedtime for Georgie", featuring Condi and Dick holding the hands of a chimp dressed in cowboy getup, and a highlighter-pink number w/ a creepily smiling Tricky Dick plastered on the front (when you achieve a certain level of infamy, you don't need no stinking captions). Other greatness: the smoke-encased revolver "Smoking Gun", a silver job w/ Kenmore's Citgo sign graffiti'd over, and, coming in your choice of teal or purple, a lower-wraparound print of a flower called "D'lions", named after those impossible-to-eradicate puff balls...that's right, the Detroit Lions.
If you're still not content, they've also got a silver or light blue print of the Jacko's childhood face/fro, and a white tee emblazoned with the black shadow of an oil rig and the words "This is why we're hot", all the more reason you need to make Progress towards the hamper.