I didn’t find it particularly offensive but thirty-some years ago a classmate of mine got sent home from high school for wearing a ‘Makin’ Bacon’ t-shirt which looked something like this.
I thought they were funny, but I’m told others find them offensive.
“I love AA meetings. That’s where all the drunk sluts are.”
“I’m not gay, but my asshole is.”
I didn’t find this one funny. I found it offensive, but more because it showed such a gross lack of creatively. “This shirt is 100% cotton and yo mamma picked it.”
I have a Rogues do it from behind t-shirt which I only wear in select company, but that’s tame compared to most in this thread.
When I was in sixth form a girl had to cover up her band shirt which simply read I am so fucking great.
I go to horror conventions, so yeah - seen some of the ones listed above - along with:
Dead Girls Do Anal (even sadder, I’m acquaintances with a guy who bought & wore this)
and
**It’s Not Rape if you Bring Balloons ** - which I was both shocked and amused by.
I know this is a zombie thread…
I know this is not really appropriate… but…
I WANT THAT SHIRT.
Reminds me of when I was with a bunch of friends, and a guy in a loud car drove by. My friend said, “You can hear how small his dick is.”
It’s not even a year old yet; you can still smell the rotting flesh!
Carry on!
I saw a guy in Wal-Mart a few weeks ago with a shirt that said “I have the dick so I make the rules” with a picture of a man hitting a woman in the face.
Yes, he was with a woman.
His mom?
She was a bit young to be his mom. I’m guessing girlfriend/wife/victim. 
A story that involves a bit of context. San Diego State University has a school mascot: Montezuma. Informally known as “Montie.”
Some people find this offensive, and there have been petitions to change it. At one hearing in front of the elected Student Council, one activist explained, in detail, why it was offensive and why it ought to be changed. He was representing a Native American student organization.
His T-Shirt read, “My Heroes Kill Cowboys.”
The arrant hypocrisy was striking.
I bet she bought him the shirt!
I remember the uproar back in 1991 when the lead singer of Skid Row wore a tshirt that said “AIDS: Kills Fags Dead”, in parody of the Raid bug spray slogan.
“Cute story babe, now fix me a sandwich”. Seen on a boy who was maybe 12. Great…future MCP in training.
We went on a trip to New Orleans and Fella was working, so I wandered around the French Quarter. I had “ahem” a few most days. It was during the week, so not as touristy as it gets on the weekend.
I saw a Tshirt that cracked me up and I had to buy it. It’s a sunny yellow T with a sweet cartoon sun and it says “Little Miss Fucking Sunshine”. I told a friend of mine on the phone about it, and she insisted she needed one as well. So I bought two.
We walked around the FQ for awhile on our last day and I wore it. Then we got in the car and started driving back to Houston. I didn’t think anything about the shirt until we stopped at a gas station to get some sodas and go to the bathroom. Small town in Louisiana.
I realize, when I see little kids and older folks and easily offended people that PERHAPS that wasn’t the best shirt to be wearing. I ended up crossing my arms over everything but the sun cartoon. (Made it hell to try to pay.)
I went to a party once, hosted by my ex-girlfriend. She was wearing a t-shirt that said “Don’t hate me 'cause I’m beautiful - hate me because I fucked your boyfriend.”
Now that’s pretty offensive in and of itself, but it was especially offensive because the married guy she was seeing at the time was there too, with his wife, who had no idea they were having an affair.
Really, I was pretty taken aback by the level of shittiness involved in wearing that t-shirt, that night, with that group of people.
I saw a guy wearing one that said SHUT UP STUPID BITCH.
It made my wonder why a woman was with him.
I saw a woman wearing this on her shirt and thought it was pretty funny:
“I taught your boyfriend that thing you like.”
I remember years ago walking up the steps to the railway station and a woman walking down was wearing a t-shirt that said, right across her chest, Stop Staring at my Tits. I burst out laughing.
This reminded me of a T-shirt I saw on a bartender which said “Yes they are and no, you can’t.”
I think I’ve found a winner. While out and about Saturday night, I saw a farang (Westerner) wearing a black T-shirt with stark white lettering that said: “Dead women don’t say no”