I recall contending with my mother over the length of my hair. All my classmates had long(ish) hair and my mother wanted me to have a buzz-cut, and I felt that I'd fit in better (i.e.: be a better conformist) by having long hair. She won for a long time.
I gave up long hair sometime during college when I realized what a nuisance hair freezing in Michigan winters was, and when I found myself closing my eyes (and feeling sleepy) when the hair kept falling into my eyes.
Frankly, keeping long hair looking (and feeling) good just means that you have too much time or money (if you're a man.) My sympathies go out to women who feel they can't wear short hair. When I was growing up, mean had to cope with the brutality of the military draft and football, and women had to cope with skirts, long hair, and child birth. Men's life has improved a little - Women's, not so much.