the difference that I see between hipster an old school is the mentality. you can be a hipster doofus all you want but old school is a mentality. I know what you mean hipster doofus are those guys with a fake horn rimmed glasses just for the hell of it with sports jacket and the beard but old school is a mentality that 1 Carries. I consider myself old school but I'm not a hipster doofus. sometimes I dress old school sometimes I dress hipster sometimes but I'm not a hipster doofus I'm old school. from my 2 cents I think it's all about the mentality ones a mentality and ones a way of life.