My high school yearbook (1982) has a photo with a football player dressed in a cheerleader uniform as a joke. I can’t describe the photo without making it sound terrible, but it’s very funny. Back then it was just considered a joke.
Today it would probably be considered insensitive to crossdressers.
In elementary school there was a talent show where one fellow wanted to dress as a girl and do some silly little show. The teachers wouldn’t allow it, because they were afraid the girls might find it sexist.