I'm probably about the furthest thing from a rebel. I wasn't even a rebellious teenager. I got into a fights with my mother quite a bit but my acting out was minimal and I've always been afraid of authority figures. Even with some of the traditional trappings of rebels like my tattoos and pink hair I don't think I'm very convincing playing the part. But sartorially you're allowed to temporarily adopt these characters. You can put on a leather jacket, heavily apply the eyeliner and pretend to hang out under the bleachers with your gang, threaten to jump someone after school, etc. All my rebellious notions might come from episodes of Freak and Geeks and my anthem might be the retro super-poppy He's A Rebel sung by The Crystals...
varsity jacket (old, similar)