I too am curious as to why a man would walk around town in a skirt but not otherwise try to appear female. Genuinely curious.
And I really am curious how it affects one's family and employment. I mean if someone sees me out and dressed, they might say "Boy that woman looks a lot like Joe.", but if I was wearing a skirt but had a beard and bald head they would say "What's the matter with Joe, parading around town in a skirt?"