so your problem is that you're somewhat anxious about everything and therefor contemplating whether it would be better to just conform in order to avoid situations that you think will only make things worse?
lo's advice is good. if you want to get more comfortable around other people, the first thing you have to do is to find a way to be comfortable around yourself. doing something just because you think that other people expect it of you is often a bad idea. if you love your long hair, love it enough that you can handle other people's comments on it. i have some social anxieties that i don't show too much, but they still exist. one of the things that made me feel better about myself was dying my hair in rather unusual colors. there's no way to stop attracting looks and comments with green or blue or pink hair, but for me that was better than the ever growing discomfort with having a common feminine hairdo.
it really depends a lot on yourself, would it be worse to stand up for your right to have long hair just because you want to, or to cut your one fairly inconspicuous way of being somewhat closer to your true self?
the comments and your insecurities aren't something that you should just get over. i think most of us know that it isn't really that easy, and it often takes a lot of reflection on one's self and what would be the lesser evil. then it's all about standing for your decision despite the hardships. not an easy thing to do, but it should hopefully end up better if we do it for our own happiness rather than just following what we think are other people's expectations.
it's also ok to conform if that makes you happier. it's not like you have to run at a certain speed, it's better to make changes when it feels right and you are able to handle it.