Dear Simple,
Straight to your question. I would think nice shirt or not. It does not bother me in the least what he identifies with. I assumed you had a specific show in mind. There is a big chance that I never heard of it. And if it was a specific point to the title of the show, I would care even less if someone was wearing such a statement.
The inconsistency in your viewpoint, is that you keep switching from clothing influencing the wearer to clothing being an identification toward the observer. To me, these are opposites. A proof or instance of one, is an example of the other being disregarded. This calls the entire idea of every type of dress has some meaning attached into serious doubt.
Traditional dress means black hat, white shirt, and so on. One who dresses like that, does so at all times, for a wide range of activities.
My take is, that types of clothing are meaningless until people unjustly put meaning to it. Just wear whatever works.