the actors i wrote about don't play any roles in order to ridicule, or if they do, it has nothing to do with a character's gender. i don't think anyone in my high school class would ever want to ridicule trans people, but the boys would still try on that gaudy flower dress which was at one time in the classroom. in dancing classes many of the girls ended up learning both the man's and woman's steps because there weren't enough boys. curiosity, necessity, experimentation and creativity are reasons i find valid enough for anyone to try on the opposite gender role even if they identify with their assigned gender. i don't know what the purpose is of every program where people try the role of the opposite gender for a limited amount of time, but i doubt many of them are made to ridicule trans people or crossdressers.
i don't mind if a guy wants to try wearing a dress, corset, and heals for a day just to see what it's like. there is a chance he might learn something about himself or others from it. that story about the model who looked seriously uncomfortable in a men's skirt is a bit weird, i don't understand why they'd use someone who's uncomfortable being associated with the opposite sex. but i've seen guys whom i believe t be cis wearing skirts with quite some confidence, no ridicule, and looking good in them.
it would probably be better for society if we had perfect freedom when it comes to clothing. anyone should be able to wear a dress if they want to, no matter what gender identity they have. clothes are only things you wear to keep warm or hide your more private body parts, they don't really belong to any specific gender other than through the norms of a given society.