I think men wearing 'women's clothes' changes by culture, period of history and status in society. When the church ruled the roost the important people in the

I think men wearing 'women's clothes' changes by culture, period of history and status in society. When the church ruled the roost the important people in the church would be wearing clothes that we recognise as robes but are essentially women's clothes. Men have cars and watches to show their wealth, in previous times garments would be more decorative for 'high value' males, with wealth to flaunt. So again 'crossing over' was possible but different. I can't think of an era where wearing women's clothes was desirable for straight male peasants though. But, for high status males, women's clothing seems to be a common thread in history and across lots of different cultures.