I feel that it is important to teach that what one wears is a choice; that one does not have to wear any particular thing because it is expected of them. One should wear a skirt, if one wishes, because one wishes to wear a skirt, not because it's ladylike, or decent, or it's forbidden to wear "men's" clothes. One can also choose to wear pants, a kilt, sorts, artfully torn garbage bags, or knickerbockers. If one chooses, freely, to dress normatively, that's fine too. I do -- but, then, I'm a guy, and my normative clothing choices are comfortable, convenient, and have pockets.
Clothing is presentation, and should be a free choice. After that, wear what makes one happy.