Women, again speaking generally, are more intuitive and emotional. Women are better fitted physically and emotionally for nurturing and rearing children than most men. Of course, these broad statements are reflective of stereotypes. But, like it or not, gender roles based on such stereotyping have developed in practically all human societies. Once such roles are in place, these same societies usually require all of their members to fit into them, and this is so regardless whether the individual members' particular personalities and physical traits actually conform to the stereotypes on which the assigned gender roles are based.
Clothing is the badge of society's gender distinctions.
It is a uniform that tells other members what they can expect from the wearer. Thus, when a male puts on a dress, he also puts himself in contra poise to major societal expectations. Doing that is not without its consequences. Society imposes sanctions if its members flout the gender roles that have been mapped out for them. If a boy isn't mischievous and venturesome, a parent might encourage him to be more so.