Will it ever be socially acceptable for more men to wear skirts and dresses?
In my view, if it were to become completely socially acceptable for men to dress in “feminine” clothes, the idea of doing so would quickly lose its appeal. There are strong taboos associated with masculinity, which demand that men strictly avoid dressing or behaving in a way that puts our masculinity in question. The possibility of breaking those taboos offers a rare and, for some of us, irresistible opportunity to act in an extremely transgressive way without actually doing any damage.
Unfortunately, while this taboo-breaking doesn’t harm anyone, it is seen by some men as a threat to masculinity in general (and their own in particular) and so may provoke an angry reaction. Therefore the transgressive appeal is offset by a need to be cautious and circumspect so as to avoid attracting masculine fury and, quite possibly, violence. That, unfortunately, is a tension I’ve never managed to resolve.