Here are some genetic women detesting the sartorial requirements of their job where some of us transgender people would love to exercise that option.
Many women in the corporate world wear tailored skirt suits and heels and then long to ditch them once at home in favour of a T-shirt and shorts. Men are much the same in abandoning the tie and stiff white shirt which for some is a type of prison. Of course not all of us are the same but my point is that we all to some degree bow to societal and corporate pressure and comply.
The expectations relative to our particular gender role have always been rigid and hence you will see only a tiny fragment of society rebel; such is the pressure of conformance where failure to comply invariably invites ridicule. Beyond clothing are also the behavioral cues which signal that this is a man or this is a woman. Here ambiguity also invites scorn and derision although that is slowly beginning to change.
If today you are a boy who dresses as a girl or a girl who dresses as a boy don't let anyone tell you different because you don't want to look back on your life one day and realize you lived it on someone else's terms.
Think how many people out there might want to escape expectation but are afraid to. Perhaps our own example of pushing the envelope will help provide them the courage to do so.