I love going into t-shirt shops and reading the walls! My favorite t-shirt was purchased at Pier 39 in San Francisco many years ago. "I caught crabs at Fisherman's Wharf". I told the shop in Steveston but they never thought it was funny. I did.
The funniest shirt I ever saw on someone wear was about 35 years ago when LGBTQ was kept quiet. We returned to a hotel in St. Croix we stayed in a few years before. The owners changed and the clientele were all gay. It didn't bother us and they were great to converse with at the pool. One guy came to the pool with a shirt "I didn't like flies until I opened one".
One of the guests staying at the hotel worked for the Washington Post. I asked if he knew Bob Woodward and Carl Bernstein and he'd worked with them! He thought it was great a Canadian followed US politics. I must admit, it's an interesting topic, especially now!