The ankle boot is a blessing from the shoe gods: they are magically versatile and surprisingly comfortable for something with a heel! While you probably already have some ankle boots in your closet-they are pretty ubiquitous-there are two essential styles for fall and winter. Must-Have #1: The low-heel, pointy-toe boot. Think of it as a modern version of a cropped cowboy boot. These shoes are casually cool and make whatever you're wearing look easy and effortless. One option is to try a Western-influenced style; a simple brown leather boot is a classic, but black suede with wrapped leather straps works too. We also like a tougher ankle boot with metal embellishments; look for something with lots of silver hardware or a menswear-inspired, double monk-strap silhouette to give your girly pieces a little edge. Styling note: the more you wear these boots, the cooler they become, so don't be precious with them! Must-Have #2: The sky-high bootie in key fall colors. In addition to your low, everyday boots, we also adore a dressier option. A high-heeled ankle boot is basically an ideal alternative to your favorite heels and it works with everything from dresses to pencil skirts to cropped jeans. In addition to basic black and super-chic midnight blue, we love richly hued suede styles, metallics, and even a statement-making pop of color. Our advice: search for ankle boots with a hidden (or visible) platform. The extra height gives your feet a little extra cushioning and insulates them from frosty streets come winter. Want some more fall fashion ideas and styling tips? Check out the Who What Wear Pinterest board that we've guest edited with some of our favorite things!