The first of the two wrestling shirts I have ever owned was a Kevin Nash one that said "Big Sexy". My teacher noticed the words and took me to the principal's office. Another kid in my class had a T-shirt on with the phrase, "Talk Shit, Get Bit." It didn't actually say shit but I think you get the picture. I told them about that shirt and the teachers seemed to have their IQ's drops simultaneously and couldn't decipher that four-letter epitaph. Needless to say, I was pissed off and they told me I couldn't wear my Kevin Nash shirt again.
I wore a Steeler shirt/Penguin shirt that said "On ice or grass we'll kick your ass" to school last year. I got called down to the office, and the principal said someone found it offensive. After about 5 minutes of arguing with him, I finally gave in and just put on my steeler sweat shirt.
When I went to..the Steelers pre-season game in August 2009, against the Bills, they wouldn't let me in because I had that shirt on. Well..not exactly they, this bitch at the front gate. I asked if I could turn it inside out, and the said no. Obviously they just wanted me to buy some 20 dollar shirt there.
Well, my uncle starts swearing the shit at them. And he just goes off, gives me his undershirt, and we go to another gate. Once we got in there I put the shirt back on. Fucking stupid though. I don't even like the Penguins, it was more of a Steeler shirt to me. I don't wear it anymore though.
Speaking of wearing shirts in inappropriate places. About 2 years ago coming back from Florida, I wore a shirt I got there with Stewie on it to the airport. I believe it said "It's your lucky day, I've decided not to kill you." I believe the lady at the security section made a joke about it when I went through, she said something like "I guess I am lucky then". I got a lot of dirty looks walking through the plane though.
Thinking about it now..I'm pretty lucky I didn't get like..stripped searched by security or something.