(FUCK YEAH DRAWFEE!!!)
LIRD I got a few rattling around lol (I have yet to make/draw 'em myself lol. Too swamped with finals and whatnot atm):
Kerberos has a single shirt with: "Women want me. Distortions fear me. Whales fear me. The Voice of Distortion and that other Voice in the light who are both my ex-bosses (well technically the latter voice is but hey both still count) have no idea what to do with me and made me immortal. And all I wanted is for my moms to love me and for one of them to come back with the milk already for fucks sake they might have disowned me without warning or reason but for fucks sake stop going on odysseys for fuck-knows-who amounts of time. It has been 20 YEARS YOU HAG!"
JièBīng has a shirt with: "Yes I have parent issues. Yes I have a license to kill. Yes I run a mercenary assassin group. Despite this, I'm still in trouble for eating the large cheesecake my coworker put in the fridge to share with everyone in the office."
Talon has a lot of stuff like these, but I'll name a few: "MY PARENTS WHO WERE ALSO AFFAIR PARTNERS MIGHT NOT HAVE WANTED ME BUT AT LEAST RAVENWOOD DOES.", "I SWEAR TO BARTLEBY IF ANOTHER FRIEND OF MINE DIES AGAIN I WILL KILL GOD AND BECOME HIM.", and "NOTHING I HAVE WITNESSED AND DONE HAS PROCESSED FOR ME YET. BUT ONCE IT DOES I WILL DESTROY A TINY PART OF THE SPIRAL IN A MENTAL BREAKDOWN WHILE BECOMING GOD." (with a bonus silly thing on the back stating "WARNING: WILL PULL A HOUSEKI NO KUNI PHOSPHOROUS IF LEFT UNATTENDED" on one of these shirts)
Akira has ONE shirt that says "IF ANYTHING HAPPENS TO THE SILLY NERDS UNDER MY WINGS I WILL DESTROY THE COUNTRY AND THEN MYSELF IN THE MOST ARTISTIC AND MEMORABLE WAY POSSIBLE." that was made by his students. He loves it dearly and has it hung on the fridge his students use for snacks & whatnot.
Choco-Berry Crisp has a few he found while rummaging around in trash bins, ft. One funny hat that also fits the bill: (In spoilers as this has already gotten so long)