You remind me of my high school self, at least in attitude. My friends and I dressed like rockstars. I'd regularly wear vinyl pants to school. We were so into Orgy, Videodrone, Margret Heater, Dropkick Murphys, Jepetto, Korn, Coal Chamber, Tool, etc. and we made fun of people who wore polo shirts and khakis from Abercrombie and Fitch and listened to NSYNC, Backstreet Boys and Britney Spears. It was just SO AWESOME when Limp Bizkit beat out BSB and NSYNC on TRL.
By junior and senior year, I made friends with people "who wore polo shirts and khakis and listened to Britney Spears and NSYNC" and realized I actually had lots in common with them, as in, the people we are on the inside.
I still swore up and down that I wasn't going to join a sorority as a first semester freshman (still had the stereotypes in my head), but I ended up having a class with several sorority women and was sold on going through recruitment when I got to know them as people instead of just labeling them.
I'm not embarassed of who I was in high school. I still love the music I liked in high school, probably because it brings back fun memories. I still love the clothes that I wore, though they packed away in a box because I can't exactly wear vinyl to work and my ass is a little bigger than it was in high school. (And I can't believe how short my shirts were back then!) I realized that the core of my personality is the same, no matter what clothes I wear or what music I listen to.
But there comes a point where you have to realize that people are more than the clothes they wear and the music they listen to. You have to find out who you are, and that shouldn't be a process of "trying on" different stereotypical personas. Just wear what you want and listen to what you want to listen to without worrying about if other people will think you're cool. When you do that, your personality will shine through.
And I don't like DMB either.
One of my friends has this funny facebook bumper sticker that reads: "I'm so indie that I saw a band by myself in an underground room and afterwards I killed them so I would be the only one who knew of their existence."