I had medium length hair, like in between my shoulder blades, but my hair looks pretty bad after it gets a certain length because it's so fine. It just gets all limp and draggly looking... but I kind of like it long. I cut it all off recently (not super short, but above my shoulders) because it was HOT (temperature wise)! And now i'm kind of sad because I miss my long hair. Not that I hate my hair now, but I do miss my long hair. And it'll be a while before it grows back out again, so yeah I'm kind of in the same boat with you. My boyfriend likes it better long but he cut all his beautiful curls off because of the heat as well so he can't give me crap about it LOL.
And as far as the more feminine thing, it kind of depends on your face, and how short you go. Some girls have a pixie-like face and can pull off super short haircuts and look gorgeous, and some girls can't. It also depends on the balance of feminine/masculine attributes about you. (this is based off of what I've noticed about myself.) If I have short hair, I don't wear baggy clothes or leave my hair undone, because then I look kind of like a guy. When I have long hair, it's cute to have my hair undone or wear baggy clothing because I have the long hair to balance it out. You know, just things like that. Not saying this applies to all people, it's just what i've noticed about myself!