One of the things that gets everyone so excited for fall weather isn’t just the gorgeous changing of the leaves to brilliant gold and crimson, the multiple opportunities for autumnal events (hello, apple picking and pumpkin carving!) or even the much-anticipated arrival of everyone’s favorite seasonal specialty (we’re looking at you, Pumpkin Spice Lattes). No, it’s the return to a style of dressing that manages to combine the best of both worlds—one part cozy and comfortable, and one part effortlessly chic—that can only be accomplished by the skilled layering of cool-weather essentials like sweaters and knits, and accented just-so by our all-time favorite footwear—boots.
As much as we love them, boots (from the lowest ankle boot to up-to-here thigh highs) pose a wide array of problems for many. Unlike sneakers or ballet flats, you can’t just pull them on with any ensemble and call it a day. Their varying heights and proportions work well—or not at all—with certain clothes, and the dizzying number of boot styles and outfit combinations can leave one’s head spinning.
But not to worry—we’re here to help. Whether you’re looking to put your best foot forward in you trustiest pair of traditional riding boots, or you’re ready to pull the proverbial trigger on a brand new, fashion-forward, over-the-knee suede style, we’ve created a cheat sheet for every type of boot, both the high heel and the flat varieties. Click through for styling suggestions that range from just right for casual weekend errands to totally on point for your next big presentation at the office, along with other helpful info like fit tips and outfit suggestions.