In the winter, we know how to wear boots: Throw on the closest pair of all-weather, snow-proof shoes and layer up eight or so times on top. But in the transitional months between deathly summer heat and holy-hell-it’s-a-tundra-out there—also known as fall—figuring out the fashion equation isn’t always easy.
The good news is that when you throw on boots, it’s no longer practically a requirement to show a sliver of ankle to avoid looking like you walked out of a late- ‘90s New York & Co ad. If an ankle bootie is your footwear of choice, just replace boot-cut jeans with wide-leg trousers, let your hem hit the middle of your boot—or even drop to the floor, letting just the front of your boot show—and you’ve got a street style look that’s majorly on-trend. Or, if you’d rather go for an over-the-knee style, don’t relegate your long coats or dresses to the back of the closet: A form-fitting boot (like this one from Zara) offers a flattering, body-con silhouette, or you can opt for a roomy style with a knee-level coat for a more advanced-style approach.
Ahead, 31 street style babes show you how to style boots of any height from now ‘til next April. Oh, and then get to shopping—here are all the boots we’re obsessed with this season.