Could this be it?
Switch (1991)
psychocat Reviewed by psychocat on . Need Help Nameing a Movie Okay,I dont know the name or whose ini t.It's from the 80's though. It's about this guy,who turns into a woman,I guess he was a chauvanist of some kind,but he has to learn how to be a woman and gets treated rudely and stuff by all his freinds and stuff.I remember one scene cause he was trying to put on a dress and didnt know how,and the sales clerk comes in the changing room and gets naked and shows him how to put on the dress. I have been looking for this movie for a Looooooong time,but have Rating: 5