I'm in pretty much the same place as the OP.
I can hide it well for pictures, but in reality, right now, my hair is so long that it is just about at my ass.
It is like this because until recently, I was not in a place in my life where I could start transitioning, and if I had to pass as female then, well, I would grow it out because I have a soft spot for really long hair on both girls and boys and thought maybe I'd like it that way (it's a pain in the ass, I tell you).
When I go out now, I braid it, the only thing I really can do.
Duo Maxwell-esque, for anyone that might happen to be a GW fan in these parts, though I don't do it purposefully to be like that.
I intend to get my hair cut, finally, to a more convincing boy-style in December, when I visit my parents for Christmas (and have hopefully lost a little weight).
I have no reason not to go out and do it right now, except, well. My mother is a professional hair dresser, and is the only person to ever have touched my hair.
She "gets me," so even when I give her crappy, "Well, I want it... like this... *waves hands, wiggles fingers, crosses eyes, makes no sense*" she just
knows. Hair grows out, but man am I paranoid about going to a random shop and ending up with something hellish and awful.
Maybe that's a sissy reason, but yeah. I've heard, and seen, the horror stories, man.
Also, just a quick touch on the "men providing" and "outdated standards" and all of that -- my grandfather was an absolute pussy and my grandmother did everything and supported everyone all on her own. She controlled the house, the rules, the income, the spending, with an iron fist.
My grandfather did not have free access to any of their money -- he was given an allowance, like a teenager. When she would send him out for grocery shopping, she would give him a specific amount to spend, and expected both the receipt and any remaining cash (to the cent) returned to her.
She had a job in law, and worked until the day she was forced to retire. He did things around the house.
They've both passed, my grandfather years ago, and my grandmother months ago... and my grandmother is still providing.
My mother received her house (the house that had always been in my grandmother's name, not my grandfather's) and generous inheritance, and I received an annuity that provides me with a certain amount of money every month no matter what.
Having lived most of my life in the house with my grandparents, I have to agree with milliontoone about "never having looked at it that way".
I don't mean to say any of the opinions or statements are wrong, just that I grew up with a different viewpoint.