Probably more complex than it appears
The reasons why we feel the need to at least occasionally dress as women are perhaps less related to the clothes themselves than to what they symbolise.
While it is the case, at least in most contemporary cultures, that women’s clothes have attractive tactile and aesthetic qualities they are not always as comfortable as are men’s clothes.
Were it the case that women’s clothes had evolved in such a way that they resembled what are currently men’s clothes, and vice versa, it is hard to believe, that the phenomenon of cross-dressing would not now exist.