the trick is to get one pair of get shoes. I would recommend a pointy toe kitten heel because they are fashionable but still easy to walk around in. Kitten heels can be worn with jeans or a more elegant outfit and in fall or spring so their pretty versatile and available; try either macys' for a more reliable shoe to keep for a while or payless if you are not much for dressing up. I would also recommend getting them in black.
I would advise not buying something outlandish and wild, stick to a simple, classic design that you can wear with several outfits. Something like a mid-heel court, in a neutral colour, depending on your outfit (and whether it's summer or winter).