How ever when men wear women`s clothing, they are thought of as very strange or even Gay? Why? Its just not fair!
Women started "appropriating" male clothing in the 1920’s, when lots of fashion rules and social rules were being broken just after WW1. "Super-feminine" dress (corsets, lace, floor-length skirts, picture hats) began to disappear, in favor of more practical, sedate clothes that women could do a variety of jobs in, and live in outside the home—then, by 1960, even womens’ gloves and hats were gone. The next step was "unisex" dressing, where women dressed in completely masculine styles (jeans, tees, sweats, pantsuits, boots, etc.)—some people think, to take on some of the "power" of the masculine elite. They were comfortable physically and psychologically, because they were identifying with male power. Some women now dress in unisex clothing their entire lives, even worrying when their female bodies don’t look good in slim masculine styles..
For a man (born into the ruling power group) to wear female clothing challenges the social order, and disturbs our assumptions.