Years ago I read an amazing essay (I tried to find it for you but couldn't sorry) that posited that hip, trendy, popular kids are that way because they worked hard at it. Figured out what makes people tick and learned to adapt. Made sure they read the right magazines and watched the right TV shows, and followed the right websites, and listened to he right music. The essayist (who claimed he was on the bottom rung on the social ladder in high school) went on to say--they worked for popularity, so they *should* get it.
He then went on to say that people say they want popularity when actually, what they want are the perks--the status and bragging rights, going to the parties, being included in things, etc.
He made the hypothesis that people work hard at the things they enjoy, so for one kid it's gaming, for another it's an instrument or drama. But a kid's interests will not necessarily be the things that catapult them to the top of the popularity food chain.
There's some flaws in the theory, for instance, a very homely kid who lacks talents will have a way harder time fitting in no matter how trendy they are.
But I still found it to be a neat theory.
(On an unrelated note, I found myself reliving the middle school years and high school as I watched my kids go through it. I get where you're coming from...)