Basically a wardrobe staple at this point, over-the-knee boots are the easiest way to upgrade your fall/winter wardrobe. While flats balance the Pretty Woman vibe of thigh-high boots, you can gain height without veering into “hooker heel” territory with a stacked over stiletto heel. Wear over the knee boots with shorts or minis to make them cold weather appropriate; team them with skirts and dresses and you can skip the tights. I also love over the knee boots with skinny jeans and a sweater — it feels just a little bit cooler than classic knee boots and makes a bigger statement than booties. Over the knee boots feel more fashion-forward and slightly sexier than a classic knee-high boot, and look dressier when worn over jeans or skinnies for a night out. Here are some of my favorite ideas for how to style over the knee boots — plus, my favorite over the knee boots for every price point.