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
