your face has the same exact shape as mine....even the dimpled chin. Your face structure is almost identical.
If you grow the sides of your hair out to cover your jawline, I am positive you will be as right as rain.
In the meantime, you can get a very lifelike wig that has that style but the sides cover the side jawlines (like a bobcut).
I do not ever say this but I guarantee you if you have your side hair hair covering the sides of your face, that encounter will rarely happen again (as trans it will always happen to a degree but the encounters will be few and far between).
Also, I don't know how you sound when you talk but if you got a feminine voice, that will always seal the deal for you. When I have a younger girl stare at me (it's always a girl between 17-27) I simply make sure I talk in front of her. It has always "convince" her I am a female (n which I am...poor semantics sorry).