Sergio Rossi Black Leather Ankle Boots (Size 8)

If you haven't checked out Rodeo Drive Resale yet, you really should, and these ankle boots by Sergio Rossi are the perfect excuse. Like a lot of resale shops or outlets, it can be hit or miss, but I think these boots are a hit. The four inch heels and pointy toes are classic, so even if the ankle boot trend falls away, these shoes will still look great with pants. The interesting, asymmetrical shape is the best part, and may prevent the leg-shortening effect of many ankle boots. They're definitely a unique style, and at $129, they'll probably go fast!