15 Fall Boots To Help You Make Peace With The End Of Sandal Season

Sandal season is pretty much winding down across Canada (single tear). And, unless you’re a devotee of the socks-with-sandals look, it’s time to start thinking about fall footwear. A stylish pair of boots is the perfect upgrade for your new-season wardrobe.
From fun, runway-inspired pairs to classic black boots you’ll wear for years to come, the possibilities are pretty much endless. Just look for a style that is versatile — a pair you can wear with cute sweatpants or a cute little dress — and well-designed for transitional weather, and the havoc it can wreak on your footwear.
Here are 15 pairs of fall boots to check out now.

At Refinery29, we’re here to help you navigate this overwhelming world of stuff. All of our market picks are independently selected and curated by the editorial team. If you buy something we link to on our site, Refinery29 may earn commission.

Ankle Boots 

Ankle boots are a popular early-fall style that look great with everything from bare legs to tights to leggings. Look for a pair with a stylish square toe or in a great autumnal colour.

Le Château Faux Suede Pointy Toe Ankle Boot, $, available at Le Château

Price in USD.

COS Square Toe Leather Ankle Boots, $, available at COS

Price in USD.

Alexander Wang Parker Boot, $, available at Alexander Wang

Chelsea Boots

Chelsea boots, which are typically ankle height, feature elastic side panels that make them easier to put on and take off. The most-fashionable pairs for fall 2020 feature a clunky-on-purpose flatform sole.

H&M Leather Chelsea Boots, $, available at H&M

Blundstone Women’s 1673 Heeled Chelsea Boots, $, available at Little Burgundy

Call It Spring Gwierwen, $, available at Call It Spring

Hiking Boots

Whether or not you’re actually planning to do some hiking this fall, there’s something undeniably cute about a pair of lug-sole, hiking-style boots. Bonus points if they have colourful laces!

Price in USD.

Danner Vertigo 917 Hiker Boots, $, available at Anthropologie

The North Face Back-To-Berkeley Mid WP, $, available at Altitude Sports

Aldo Jollyra, $, available at Aldo

Rain Boots

For drizzly fall days, there’s nothing better than a pair of well-insulated waterproof boots. Basic black is great, but this season there are several colourful takes on the classic Wellington to consider.

Hunter Refined Slim Fit Short Rain Boots, $, available at Hunter

Zara Low Heel Rubberized Boots, $, available at Zara

Lemon Jelly Layla 02, $, available at Jean-Paul Fortin

Black Boots

Speaking of basic black… a sleek pair of black boots for fall is never a bad idea. Options abound in both leather and faux — it’s just a matter of picking between shimmery and matte finishes. (Decisions, decisions.)

Price in USD.

Brother Vellies Brandy Boot, $, available at Brother Vellies

Zvelle Classica Boot, $, available at Zvelle

Matt & Nat Deena, $, available at Matt & Nat

Knee-High Boots

From preppy riding boots to heeled, retro-inspired suede boots, the knee-high is a late-fall classic. If shopping online, remember to double check the measurements to make sure that the calf width and boot height will work for you. As a petite gal, I’ve definitely bought knee-high boots that were much too tall for my legs!

Banana Republic Leather Mid-Heel Boot, $, available at Banana Republic

Sam Edelman Penny Boot, $, available at Nordstrom

Mango Leather Boots With Tall Leg, $, available at Mango

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