Well, there is a long and proud history of songs that celebrate cross-dressing, usually in one of two categories:

1. Intentional, such as the all-too-common songs about lasses who had to dress up as lads to do some heroic deed or other (examples: Famous Flower of Serving Men, Handsome Cabin Boy, etc.)

2. Unintentional, such as all those songs where some poor sailor is lured into a woman's room, is drugged, and awakens nude in an alley the next morning, having to grab whatever he can find (usually a dress or apron or other woman's garment) and sneak back on board ship.