This compound subject, therefore, requires a singular verb to agree with it. SUBJECT-VERB RULE #2 Two or more SINGULAR subjects joined by or (or nor) act as a singular compound subject and, therefore, take a singular verb to agree.
For example, You can't help but see how he feels about her; he wears his heart on his sleeve. Shakespeare had it in Othello (1:1): But I will wear my heart upon my sleeve for daws to peck at. People who wear their heart on their sleeve express their emotions freely and openly, for all to see.
and I think the best answer is That you're wearing an Affliction shirt. You go one to state that the more appropriate statement is what do you hope people will think of you for wearing [the Affliction shirt]? I guess I am just not as into shirts defining people or their personalities as you are. I don't think that a shirt says anything about someone (unless it has something legible on it, e.g., the I *heart* to fart shirt I've seen photos of Bert Blyleven wearing--I actually do believe that he enjoys farting, but then again maybe he doesn't).