I have so many like this. I especially hate when I buy a shirt I really like, and then when I wear it once, someone either says "I have that shirt too!" or "That shirt reminds me of [insert something stupid like Twilight]" which totally ruins the shirt for me.
I have several. Some are from my school, and two are inside jokes.
There's nothing I wouldn't wear in public...
I have this one tye-dye shirt that I got like, five years ago is pretty much falling apart. I only sleep in it.
Most of the shirts I don't wear in public are badly stained.
I have this one and I would never wear it around mostly because my family would force me to explain the shirt and then when I did they would absolutely hate the shirt and then disown me. But I'd wear it around other people, definitely.