I have always wanted to try to pull off high heels, but they seem a little bit old for me...if that makes sense. I feel like if I wear them I would look...stupid. When you girls and guys see a younger teen wearing heels, what do you think? Not stripper heels but like these link
I think those heels are a bit too dressy. Maybe starting out with a black patent pump or nude heel would be best if you're just starting out. I stay away from heels because I'm already 5'6" and can't walk in them to save my life.
Make sure you're wearing the right jeans (straight or skinny cut) too to dress them down. I'm sure you can pull it off then.