How to Wear Ankle Boots Now: Your Complete Guide

Ah, the ankle boot, that perennially stylish wardrobe staple that you return to time and again whenever the temperature outside starts to drop. As much as we love our timeless ankle-hugging friends, it can be challenging to come up with fresh ways to style them. There are only so many times you can wear the same skinnies-and–ankle boots combo, right?

To that end, we’ve scoured the street style world far and wide to dredge up some ladies who gave the footwear staple new and exciting spins. Whether they're mastering the art of layering pretty dresses over jeans or bringing their casual outfits to truly stylish new heights, fashion girls are teaching us valuable lessons in how to wear the ankle boots we know and love. Take note, readers! These cool outfits bring the best of this season's ankle boots. Copying them all is highly encouraged. Keep reading to discover 16 fresh ways to wear ankle boots right now, and shop the coolest pairs!