Yeah, I don't really mind the transvestites if they know they are men and don't try to make other people say otherwise, unless they are applying for a job in sales or childcare, I care not and even then might be able to be persuaded otherwise.

Men wore dresses in medieval times because pants are harder to make than a simple dress, goes for both cloth and armor. The Greeks thought pants effeminate for some reason (My best guess is that since Ancient Greece was a warm pre-AC environment, it stemmed from probably making your balls sweatier), and it was a minor scandal that Alexander started wearing them.