26 Pairs Of Ankle Boots At Every Price Point

Like a great pair of jeans or a timeless trench coat, a versatile pair of ankle boots is essential come fall. Whether you pair them with a little black dress or with a moto jacket, the perfect pair will see you through unpredictable weather and chilly days in style. From basic black booties to trendy square-toed silhouettes, lug soles and textured leather, we’ve rounded up all the coolest styles to wear this fall—including options from some of our favourite Canadian brands.