These Are the Best Boots to Shop This Fall
It’s time for everyone’s favourite part of cozy-season dressing. From ankle boots to wide-calf knee highs, here are the best pairs to shop and style for fall.
After savouring sunny afternoons and temperatures above 20 degrees well past mid-September, fall’s official arrival has finally convinced me to make the switch. My strappy summer sandals and peekaboo kitten heels—both summer mainstays—have officially gone into hibernation to make way for more seasonally-appropriate footwear.
Saying goodbye to summer always comes with a twinge of bittersweet nostalgia. I, for one, am not ready to say goodbye to sun-soaked poolside afternoons and breezy linen separates just yet. But just as quickly as that wistfulness settles in, I’m reminded of the true saving grace of the upcoming cozy season: my carefully curated collection of boots.
After all, nothing signals the start of fall quite like slipping on your trusty, go-with-everything boots for your first (or fifth, no judgment) pumpkin spice run of the season.
It’s an undisputed sartorial fact that boots are the ultimate fall footwear staple. They’re practical yet endlessly chic, seamlessly pairing with everything from a casual jeans-and-sweater combo to a polished mini skirt with tights. They’re also incredibly versatile. The right pair can just as easily be the star of your outfit as it can silently elevate an ensemble under a pair of flared trousers.
However you prefer to style them, there’s a boot out there to fit every outfit, occasion and mood this season. Whether you’re looking for reliable Chelseas or are ready to venture into the world of knee-highs (wide calf girlies, be not afraid!), we have plenty of stylish picks for you.
Ahead, discover the best boots of Fall 2025, featuring styles so polished you’ll want to slip them on before the leaves hit the ground.
Chelsea boots
Classic, comfortable and oh-so easy to style, it’s no wonder why the beloved Chelsea boot has been a fall footwear staple since its popularity exploded in the 1960s. Defined by elastic side panels and an ankle-skimming silhouette, the style effortlessly balances form and function. Whether you gravitate toward a chunky lug sole for a more grounded feel or prefer a sleek leather version for everyday polish, the Chelsea boot is a silent powerhouse with unmatched versatility.
Ankle boots
If there’s one style that truly does it all, it’s the ankle boot. Sharp and unfussy, it works with just about everything in your fall wardrobe. Go classic with a sleek black leather pair like those seen on Alexander McQueen’s Fall 2025 runway or have fun with bold colours, glossy finishes and unexpected details that add just the right amount of autumnal edge.
Knee-high boots
My personal favourite, knee-high boots elevate any outfit (often literally) with their sleek silhouette and inherently polished feel. This season, designers at Dior and Gabriela Hearst pushed boundaries with unique styles and bold prints that played on the boots’ traditional form. On the other hand, Ralph Lauren and Hermès proved that classic, neutral-hued knee-highs will always reign supreme. Whatever style you prefer, it’s undeniable that these boots are the ideal companion for crisp autumn days and refined cold-weather dressing.
Wide-calf knee-high boots
If you’ve never been able to find a knee-high style that truly fits just right, this category is for you. Designed to give your legs a little extra breathing room, wide-calf offerings make all the difference when it comes to fall footwear shopping. Plus, the wider-shafted look is trending this season, with Fall 2025 designs from Burberry and Coperni leading the charge for sleek yet spacious styles.
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Stephanie Davoli is the editorial assistant at FASHION Magazine. With a passion for all things fashion, beauty and pop culture, she’s inspired by fashion psychology, sustainability and industry innovations. Her previous bylines include The Toronto Star, Chatelaine and The Quality Edit. When she’s not working, you can find her shopping, taking a Pilates class or combing through the Vogue archives.
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