You can change his haircut slightly but he still looks the same and if you're still needing to take classes, prefects in the school wi ll bust you if you're not in uniform so it's like a disincentive to wear anything else. The customization is really lacking on Jimmy. Even when you're done with classes though, it's a constant race against the clock to finish tasks before you pass out at night. Early in the game, you'll either be getting chased around campus for being truant from class, or you'll be spending the whole day in class (Thankfully that stops when you complete the entire course and it lets you skip that particular class).
Upgrades from taking courses or doing missions or side activities definitely make it all worthwhile. Tons of stuff to do with plenty of interactivity to the general environment.