Could this person be someone who is new to crossdressing and really didn't have anyone to help them with presentation? I know that most of us see one thing in the mirror but in reality it is really not the truth and not what other people will see. I like to wear sexy clothes but I really don't look very sexy in them. Some of the things I wear are not age appropriate but if I ever pick up the nerve to out I may be guilty of wearing some of them because it is all I have. Maybe it was the day he picked up the nerve to out in public for the first time and what he saw in the mirror was enough to make him feel like he could pull it off. I applaud him for having the courage to go out and try. That is more than I can say for myself.
Jeannie