I once went to a "come as a member of the opposite sex" party as a Scotsman, as it was the only time the rest of the group would see me in a 'skirt'... My BF went in miniskirt and fishnets, and shaved the beard off for the evening, and was the most convincing girl there - all the other blokes were rugby types with hairy shoulders and off the shoulder gowns... <bleaugh>
Couple of weeks ago I was out with a chap and I wore a dress, and got so fed of his "You should wear a dress/skirt more" that I resolved a) to wear what I damn well like and
probably not to see him again...