If you want to try new hair then by all means do it. Because YOLO and all.
And yeah, I've always hated my hair, too.
I'm thinking of trying a long on top, short on sides and back look.
BTW if you suffer from looking extra young like I do, try pushing your hair back off of your forehead. I gain/lose ten years depending on whether my hair is pushed back or drooping down. It naturally falls forward if I don't 'train it' to stay back, though.
If you have a non-oval shaped face this might also be of interest to you: