One idea ive seen before and always found interesting was ''crossdressers through the ages''. So beginning at the beginning, the prehistoric time with cavemen. Pretty much just rocks and leopard print.
I'm not sure if I'll do other times as well, as I don't just want to put guys in outfits from the time but make an outfit that represents the time or references parts of the time. So for example instead of a princess for the medieval times, I would probably do a knight armor dress instead. mixing the knights and princesses of the time into one.