There are many things I'm wrong about. One of the few that I will deem a "do not challenge me on" is how classic a black bootie can be. Certainly there are ways to make this shoe edgy, preppy, sexy or modern; however, it's very hard to wear the look wrong. Above are some of my favorite black booties. Wedges, heels, buckles, gold, and Western influence. I'm swooning over the Rag & Bone pair you never seen before (kidding). Below are a few more of my favorites: