There's a fantastic "meme" (I hate that word) floating around, and a bunch of illustrators have drawn themselves as teenagers. You can see the complete list of entries here- it is waaaaaay too much fun!
Many of the other contributing illustrators seemed to be geeky in the Kool-Aid dyed hair, Doc Marten & choker-wearing sense. I was geeky more in the "cried-because-I-got-a-B-in-French class" sort of way. My friend Anne will be more than happy to tell you that story. (BTW, HAPPY BIRTHDAY, Anne!)