This is funny.
I was sitting in class last year and in walks this guy with some purple pleated skirt and all the trimmings.
I said nothing; I didn't stare, it was weird.
The professor didn't see what he was wearing as she came into the lecture room after everyone had been seated.
Coincidentally he was asked to come up and work a problem on the board.
Before he got up he said to the professor..."Okay I'll come up and do the problem but don't laugh at me. My girlfriend asked me to dress as a woman today for halloween and she's dressed like a man."
Suffice to say I thought it was cool; prior to his explanation though...it was weird.
No; if my wife asked me to dress in a dress I would not do it.