18 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 to transition from fall to winter. Whether you pair them with a little black dress or 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 metallic leather, we've rounded up all the coolest styles to wear right now.

Maguire

Boots, $245, maguireboutique.com

H&M

Chelsea boots, $50, hm.com

J. Crew

Ankle boots, $394, jcrew.com

Reformation

Mini western boots, $565, thereformation.com

Sorel

Shearling booties, $230, sorelfootwear.ca

Mango

Pointed heel ankle boots, $70, shop.mango.com

Cougar

Waterproof leather boots, $190, cougarshoes.ca

Poppy Barley

Lace-up booties, $365, poppybarley.com

Aldo

Patent platform boots, $120, aldoshoes.com

Ugg

Platform boots, $209, urbanoutfitters.com

Dr. Martens

Platform Chelsea boots, $200, drmartens.com

Zara

Metallic leather boots, $149, zara.com

Everlane

Square-toe boots, $401, everlane.com

Hunter

Chelsea boots, $165, hunterboots.com

La Canadienne

Leather Chelsea boots, $550, lacanadienneshoes.com

Simons

High-top Chelsea boots, $229, simons.ca

Steve Madden

Lug-sole Chelsea boots, $140, nordstrom.ca

Vionic Shoes

Waterproof lace-up boots, $230, vionicshoes.ca