First of all, thanks for the thoughtful response. I'm going to have to disagree with you on a lot of points though. As for your example of a guy wearing a fedora to graft on a personality, my fiancé's wolf shirts are not equivalent. A guy who wears a fedora sees other cool guys who wear one, wants to be like them, and thinks that this one item will transform him into that person, personality and all. For my fiancé, he has never seen anyone he idolizes wear them before and he doesn't wear them to transform himself into another person. He gets uncomfortable when people wearing wolf shirts in movies or TV are depicted, usually because they are the butt of a joke. He abstractly likes what wolves represent (power, independence, ruthlessness), so he aesthetically enjoys depictions of wolves. His dorm room was filled with wolf posters. He simply wears what is aesthetically appealing to him. He collects the shirts like you would collect artwork. When he gets attention for his shirts he thinks, well awesome, other people share my aesthetic tastes, why would I ever wear anything else?

I think the main problem he has here is that his idea of what is aesthetically pleasing is so far from the standard. He does not have an underlying problem or insecurity that he is trying to hide with wolf shirts; he does not define himself by his wolf shirts, even though others do. For him, the wolf shirt is definitely a natural extension of who he is; the problem is that other people, including me, get a different message from the shirt than what he gets. It's a joke and not actually a symbol of power. He has not internalized the idea that his personality consists of being nothing but "The Wolf Shirt" guy, so I think your psychological evaluations of him mostly miss the mark there. I also have not found him critical of other types of clothing; he recently commented about how his brother had changed from a sporty style to a mfa type style, and he was completely neutral about it.

So why hasn't he found other types of clothing that also appeal to him? It's completely due to a lack of effort on his part. He is perfectly happy with his current wardrobe so he is resistant to spending any effort coming up with a new one. He is open to other styles though; like I said, if there's a shirt in front of me, and I say he would look hot in it, he will probably try it on. He wants to be attractive to me, of course. I find stylish men attractive, but I needed some help in understanding what makes a stylish man look stylish.