So one thing that I’ve noticed is that cross-dressing tends to be both handled and looked at differently for the different genders. No one really thinks too much of a girl putting on pants, though I can think of a few movies or comics where the issue was brought up, but a guy putting on women’s clothes? That’s a whole different story. In fact, if movies, games, books, everything ever, is to be believed, men dressing up as women is funny.
I theorize that this may be because society still looks at men as being normal and at women as being something else. We see this a lot in media, and the same can be said for a lot of portrayals for the sexes. Even the whole idea of what constitutes a strong female character may be skewed to a portrayal of a woman who partakes in things that society considers inherently masculine. Of course, this may also be because most things are run and written by men.
One person, windupviolin, theorizes that this may also be because women are seen as less important than men, from society’s point of view. And because women are less important, our clothing choices are less important. But society has placed so much on the male role that it tends to stick out to us more. If you click the link at the start of this paragraph, you’ll find a bunch of pictures of men and women sharing each other’s clothes. Notice that your eye will more than likely be drawn to the man.
Whatever the case may be, however, it is still common for people to portray male characters dressing up in women’s clothes as humorous.