As far as teenybopper pop stars go, Taylor Swift is probably one of the best. Her songs are catchy and filled with the kind of lyrics you would have written on your high school notebooks.
Here's some advice, teenage girls: if a dude only wants to date you because you've taken off your glasses and dolled yourself up enough to compete with his cheerleader girlfriend, kick him to the curb. It's not worth selling yourself out to someone else's standard of beauty to date some superficial jerk. Yes, high school is rough, and yes, looks play into it a lot, but trust me: beauty does not come from a dress or a pair of contacts or a trip to the salon. It comes from knowing yourself and loving yourself and all of that good stuff. Perhaps instead of wishing a boy would see you in your glamorous glory, you should try to surround yourself with people who see you for who you are, and think you're beautiful no matter what.
Oh, and just wait until you see Hunky McHighschool five years after graduation. You'll be glad that you had your awesome specs on to see right through him.