My then-teenage brother once went through US immigration wearing a t-shirt branded with the initials of the then-popular brand, French Connection UK.
Needless to say the US immigration officials took some offense and asked him a bunch of questions. I'm not sure they realised it didn't say what they thought it did, even after we explained about French Connection.
The dyslectic f*ck brand was and still is annoying. In Melbourne AU they had a 20 or 30 metre tall logo covering an entire wall of an industrial building. Very glad to see it gone.
A friend of mine got pulled aside for extra questioning at Newark in the mid-90s because he was wearing a t-shirt that proclaimed "Smoke me a kipper, I'll be back for breakfast". I think the officer presumed it was some sort of drug reference.
Needless to say the US immigration officials took some offense and asked him a bunch of questions. I'm not sure they realised it didn't say what they thought it did, even after we explained about French Connection.
These were obviously simpler times as I also as a teenager once went through US immigration wearing a Threadless Community Party t-shirt: https://www.threadless.com/product/383/the_communist_party