Hmm, this question could be up for debate. When you think about men wearing skirts/dresses, what comes to mind? They are gay, right? Men who choose to be "fashionable" may just be fulfilling a fantasy of theirs. Have you ever thought about the Scottish? Scottish men wear kilts. Other cultures allow for men wearing skirts. In the movie Tootsie, a man wore a dress. Same goes for Mrs. .