Well, SoftShocks, looks like you have yourself the beginnings of an answer there.
There's a whole rainbow of gender identity/expression to be had. There are people who fit the binary, people who are masculine women, feminine men, agender, bi-gender, gender fluid and transgender people, both mtof and ftom who run the gamut of expression, themselves.
The decision to transition isn't a question of fashion. It has more to do with one's relationship to one's own body. It is a difficult, life-changing path that is usually only undertaken when one's body does not match one's mental gender. If you're not experiencing the mismatch, there isn't much of a point in it.
So, wear what makes you happy and keep in mind that there are plenty of items of clothing that are considered women's wear that used to be men's wear historically and vise versa, that most of what we consider to be gendered clothing is arbitrary anyway. Wear what ya like and rock that shit!