I always thought the coolest teenager ever was Claudia from The Babysitters Club. She was so fashion forward. Check "What Claudia Wore" here. Its a perfect homage to her creative genius. The author is not always complimentary of her taste, but it is pretty funny stuff to read if you were into TBC like I was- she includes lots of excerpts with her own running commentaries of them.
Now, after that, we are going to move on to my teenage era- the 90's. For shame.
Its very unfortunate that my teenage years were the years of flannel (per "My So Called Life.") I had no chance to let my hair down like Claudia did in the 80's.