we were the issaquah indians, so our senior shirts said "chug-a-broo tribe" and then on the back there was a hippy indian drawing, and he was leaning on a mushroom smoking a joint.
we got to wear them, they started telling people not to wear them after about a week, but rules have gotten a lot more strict in the past couple of years.
^the above idea was one that we did for senior skip day, where on the back was a picture of all the kids at the skip day kegger.
also we had gym shirts, that you're supposed to write your name on in sharpie in this little name box, like the ones on napolean dynomite, and people did all sorts of drug/alcohol references...back then people just didnt care as much. god im old.