Long hair; didn't even have to try and hide it.

This was my version too. No fro, but longer hair.

CD player or iPod would be in a back or side pocket.

That's why I wore a hoodie. Had the headphones in the seam of the hood

I just did the thing where you drink vodka in the parking lot with the Polish kids at lunch so you don't care about having to sit through class.

Similar - I had a big interior pocket and I ran the cord through the lining and into the space where my roll-up hood should have been. Except that I'd cut away most of it such that my crappy walkman-knockoff headphones (broken off from their frame) were inside each tip of the collar, right next to my ears.

I rarely used it in class and when I did I kept the volume really low and smashed it to my ear similar to the pic. Mostly I think I was just a teenager and wanted to feel like I was getting away with something, I think.