If you want pointers on buying the perfect pair of sneakers, we've got you covered with an entire SYW on the subject. Buying dress shoes is slightly more complicated. Sounds hefty, but remember, quality over quantity. You can wear the best outfit in the world, but if your shoes suck, you might as well be wearing a potato sack. He also says, ideally, your shoes will match your belt which will match your briefcase.
Nothing looks worse than a brown belt worn with a black pair of shoes and a tan briefcase.
Except if all three are covered with hearts and unicorns. If you can only afford to purchase one more pair of shoes, Stan prefers that you go with a black leather boot. This way you can wear them both for work and for going out at night. If you are morally opposed to boots, Stan's suggested alternative is a pair of nice leather slip-on shoes. These shoes are sort of loafer-ish, and they have a high vamp that covers your socks.