forest1985 said:
clothing as being feminine or masculine is culturally relative and personally subjective; why does wearing pants not get all "female" characters labelled crossdressing, while "male" characters do? why are high heels "feminine" and cowboy boots "masculine"?body types as masculine and feminine are also subjective and culturally relative, for example a slim, skinny build is more feminine in western cultures, while in the east (specifically, japan, south korea, china and places where those countries are the main cultural imports) it's a beauty standard for all genders. Long hair is seen as more feminine, but in many cultures it is not. Most native american cultures see the hair as an extention of the soul/self, and it is a taboo to cut it, same with some pacific and african cultures. being strong, muscular and whatever is not always masculine; in some cultures it isn't tied to feminine or masculine presentations, and in others it's more feminine.
I mean, yes, at the end of the day all of this stuff is arbitrary social constructs with no objective basis, but we're trying to run an archive categorization system here. How we tag "man in dress" is in fact an important question, because people want to search for it. If you don't like calling that crossdressing, you're welcome to present an alternative, but do need some way of referring to the concept.