That’s got to be the winner of the thread in terms of “amount of courage/stupidity needed to wear it”.
Dirty Dick’s, A big seafood chain on the Outer Banks of NC has T shirts that say “I got my crabs from Dirty Dick’s”.
I saw a young guy in a rather rednecky bar wearing a shirt that said Jesus is a Cunt. No one bothered him, but he did seem to know a lot of the regulars.
The slogan on our band shirts is our name in the Jack Daniels logo and the caption When You Just Don’t Give a Fuck. Nobody comes to our shows, but we sell a lot of shirts!
my grandfather moved to the beach. He was a conservative man, and frugal - a veritable survivor of the depression. So, of course, he beachcombed in the mornings. Frequently, he would pass to the grandkids his findings (generally, clothing which we could wear).
He once gave me a shirt which stated on the front:
Chinese 69.
The back: Chu Man Chu.
My mother divested me of this treasure in short order, needless to say.
On the topic of inappropriate gifts not understood as such - when my kid was an infant, my mother happily gave my wife an infant T for the boy that said “Chick Magnet”. She had no idea what it was intended to mean (in her head, she had a vision of cute little baby chickens following the kid around).
Not as offensive as the others above, but not destined to be worn, either. 
Another new entry - Skateboard Company -- Backlash Over Asian Slur T-Shirt ... 'G**ks of Hazzard'
I always thought a shirt with “Co-Ed Naked Solitaire” would have been pretty funny.
“Jesus is a cunt” shirt. The kid in the photo with him just adds that extra bit of offensiveness.
“No hole is too deep or too sloppy.”
This one doesn’t even try for humor. “I hate queers.”
Or you can just scroll through all of these from People of Walmart.
It’s a shirt from the black metal band Cradle Of Filth, a friend of mine has it. She used to wear it a fair bit.
I prefer my Dimmu Borgir “Religion Sickens Me” shirt, as it gets the point across without being needlessly crude. No doubt, plenty of people would take offense at it.
I’ve also got several shirts with inverted crosses that people have got mildly offended by before. And, ironically, at least two with normal crucifixes (one Black Sabbath, one Nightwish) that other black metal fans have called me on for wearing!
Oh, there’s also the Burzum shirt with the picture of the burnt out shell of one of the churches burnt down by various Norwegian black metal types (he didn’t burn that particular one down himself, as far as I know). I’m sure people would get upset at that if they what it was.
When I was at a Ryan Adams concert last year I fell in love with and purchased one of his pentagram shirts. The pentagram is pink, and it’s circled by ‘Ryan Adams’ in some kind of metal font. I thought it was the most ironic (yet fitting) thing I’d ever seen and had to have it. I love everything about the shirt… except that I don’t dare wear it.
That is an awesome shirt! The metal font is very similar to the one Iron Maiden use for their logo, so pretty iconic.
He is a HUGE Iron Maiden fan, and a metal fan in general. That’s why the shirt was fitting while being highly ironic because, well, it’s Ryan Adams.
Back: Say yes
When my nephew was an infant, I bought him a t-shirt that said “They Shake Me!” and some tight-asses that saw it got all bent out of shape…
My cousin had to have a double ‘modified’-radical mastectomy a few years ago and barely survived. She finally had her final reconstructive surgery last October. I gave her a t-shirt that says, “Yes, they’re fake. The real ones tried to kill me!!!” right across her boobs. She and her friends laughed until they cried when they saw it. But the first time she wore it out, she was accosted by some evil bitch (rhymes with RUNT) in Whole Foods and berated for being so flippant about something that kills more women than blah, blah, blah…(she lives in LA, so you can imagine the type)…
My cousin, who had always been polite, mild-mannered and non-confrontational (even in LA, she was a proper Southern Belle), responded with, “If I had a dick, this is where I’d tell you to suck it!” and walked away…
Not offensive, but I always like the T-shirt from a local bank that had the bank and then the words:
We do it with interest!
Then in small type:
Penalty for early withdrawal
I think I’m in love with your cousin. She rocks.
She’s awesome, and a total BABE, too…she’s 15 years older than me (and only five years younger than my mom) but I always had a HUGE CRUSH on her when I was growing up…which would be kinda creepy/gross if I were of the heterosexual persuasion. =)
I have no clue how to post a photo but here’s a link to a photo of her on her 50th birthday… JOY
She lives in L.A. and everyone she knows is in the tv industry (including her husband), so she has no reasonable expectation of privacy… :D:cool:
The first image that gave me was a chick with a dick {shudder}. Probably not what was intended.
That was the Little Shop of Horrors, right?