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It's finally starting to cool off for fall, which means boot season is officially back. Whether you live in cozy sweaters or are still hanging onto your favorite denim skirts, nothing anchors a fall outfit quite like the right pair of ankle boots. From rugged weather-ready hikers and chic Western heritage styles to sleek pointed-toe silhouettes, we’ve rounded up the 14 best fall ankle boots to elevate your rotation this season. Step into the new season in style and find your new favorite pair!
Scroll for our favorite ankle boots for fall!
Free People
Blundstone Classic 550 Chelsea Boots
These classic leather Chelsea boots are the go-to for everyday wear. They feature a pull-on style, elastic side accents, and a cushioned footbed for all-day support.
Old Navy
Old Navy Faux-Suede Chelsea Boots
For a budget-friendly option, these faux-suede Chelsea boots are actually really comfortable and combine timeless style with easy slip-on comfort for chilly days.
Madewell
The Ryder Ankle Boot
These suede loafer-inspired ankle boots from Madewell feature a penny strap and durable rubber lug sole. Complete with MWL Cloudlift Lite padding for wear-all-day comfort, they're the ultimate combination of polish and practicality.
Toms
Toms Delilah Buckle Ankle Boots
The striking hardware on these brown suede ankle boots brings the perfect amount of edge to your seasonal wardrobe. Show them off alongside a denim mini skirt or pair them with your favorite jeans for an instant style upgrade.
Free People
Free People Brayden Western Boots
Bring a touch of rugged Western heritage to your rotation with these standout boots. Combining classic craftsmanship with breezy bohemian flair, they anchor any fall outfit with unmistakable character.
Madewell
Madewell The Lexie Ankle Boot
These suede boots feature a tapered square toe and stacked block heel. Versatile enough to wear with everything from denim to midi skirts, they feature updated design tweaks—including a shortened toe and inside zipper—for an even better fit.
SeaVees
SeaVees Bolinas Off Shore Boot
You can take these ankle boots anywhere this fall, as they are totally waterproof and built to stand up to the elements with style. Plus, the white color shakes things up from the expected rotation of browns and blacks!
Anthropologie
Maeve Snip-Toe Heeled Boots
Defined by crisp cuts and playful polish, these Anthropologie-exclusive boots feature a pointed kitten heel, pull-on styling, and a sharp snip-toe silhouette designed to instantly elevate any look.
Hunter
Hunter Gemma Waterproof Suede Boots
Built for city streets and beyond, the Gemma is a confident suede ankle boot featuring a chunky silhouette, front zip closure, and a bold lugged outsole. It delivers steady footing across wet pavements while keeping every step cushioned and comfortable.
SeaVees Salt Creek Boot
A Chelsea boot built for adventure and everyday style, these cuties feature a gorgeous water-resistant leather upper, Vibram outsole, stitched welt, and leather lining, it is versatile enough for year-round wear.
Anthropologie
Jeffrey Campbell Joshua Tree Pointed Toe Booties
Featuring a sleek leather upper and insole, side zipper closure, and a sturdy block heel, these fashion-forward booties from Jeffrey Campbell effortlessly balance trend-setting aesthetics with everyday walkability.
Anthropologie
Maeve Cap-Toe Stretch Ankle Boots
Cut from a smooth leather blend, these sleek ankle boots feature a striking pointed cap-toe detail and a low, structural block heel. Gorgeous!
Free People
Jasper Hiker Ankle Boots
Somewhere between a loafer and a boot, these fall ankle boots were born. The contrasting stitching that surrounds the shoe is so cute, and you get even more pop from the color-dotted laces. The chunky soles balance out the look while still being very practical for hitting the pavement!
Tecovas
Tecovas The Daisy Boot
These sturdy ankle boots from Tecovas are crafted with high-quality cowhide leather to last your looks years and years.
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