I've been going to a chain salon like super cuts. Should I find a high class salon or find a barber?
It depends on what you want. If you want something stylized, then youll likely need to find a place that can do that. I think youd look much better by simply having a barber or a friend (or yourself) get a hair clipper, stick a 3/4 to 1 inch attachment on it, and go to town. Now, you wont be considered stylish, but your hair will look fine and 'grown-up' looking, and youll save a shit ton of money too