23 Ankle Boots to Buy Now and Wear Forever

Practical, durable, and stylish to boot.

ankle boots
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You'll find at least one pair of ankle boots in every woman's closet, and for good reason. Yes, you can sport them in the summer, '90s-style, underneath your cottagecore frock or your slinky slip dress—but ankle boots really take center stage in the fall and winter, when temperatures begin to drop and denim becomes a mainstay. Whether you favor functional silhouettes engineered for the outdoors, cozy interiors, or refined leather styles, there's a heel length, a sole construction, and a bevy of embellishments for just about any fashion play. As Pre-Fall selections begin to roll into stores, consider investing in a pair (or two) that you can test drive now or live in for fall/winter. We've hand-picked our favorites.

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1460 Pascal Boots
Courtesy of Dr Marten's
Dr. Martens ssense.com
$83.00

Add a bit of flower power into your fall boot arsenal with these '90s-inspired Dr. Martens.

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Nina Leather Boots
Courtesy of Sam Edelman
Sam Edelman saksfifthavenue.com
$150.00

The minimalist white ankle boot dominated the fashion scene last season. We foresee the same trend taking over this Fall.

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Chevonne Sheepskin Waterproof Boots
Courtesy of Ugg
UGG saksfifthavenue.com
$60.00

These sleek sheepskin-lined ankle boots will  take on puddles and wet fall leaves with ease.

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Bridget Chelsea Combat Boot
Courtesy of Loeffler Randall
Loeffler Randall loefflerrandall.com
$395.00

Slip into these stretch knit ankle boots that will look equally polished with a dress or ankle-cropped jeans.

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Emelie Short Lace Cozy Boot
Courtesy of Sorel
Sorel sorel.com
$102.00

You don't have to sacrifice practicality or style. These waterproof ankle boots will look smart while combatting the elements.

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Tux Loafer Boot
Courtesy of Chelsea Paris
Chelsea Paris chelseaparis.com
$450.00

Add a black-tie spin to your everyday ensemble with these patent-leather, square-toe-boots that take inspiration from formal wear.

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Chunky Sole Ankle Boots
Courtesy of Camper
Camper farfetch.com
$159.00

Fall camping trips just got cuter with these contrast sole ankle boots in a poppy red hue.

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Women's Ankle Boot
Courtesy of Gucci
Gucci gucci.com
$980.00

A soft merino wool lining will keep your feet extra cozy, while a rubber sole deems these slipper-esque shoes safe for outdoor wear.

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Lug Sole Chelsea Boots
Courtesy of Proenza Schouler
Proenza Schouler fwrd.com
$825.00

Trade out your worn-in suedes for this rugged, yet refined pair. Take care of them correctly, and you'll have them for years.

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Kolbie Lace-Up Boots
Courtesy of Stuart Weitzman
Stuart Weitzman farfetch.com
$964.00

Take a closer look at these tough-looking boots and you'll notice sweet details like feminine gold eyelet detailing.

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Croc-Embossed Leather Combat Boots
Courtesy of Schutz
Schutz saksfifthavenue.com
$74.25

A studded sole infuses edge into these croc-embossed, rubber sole ankle boots.

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River Boot
Courtesy of Dear Frances
Dear Frances verishop.com
$575.00

Say hello to your new, very versatile. everyday ankle boot. 

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Chain-Link Ankle Boots
Courtesy of See by Chloe
See by Chloé farfetch.com
$492.00

Not all ankle boots are made equal, case in point: these fringe-faced ankle boots that come decorated with statement gold hardware.

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Hemp Combat Boot
Courtesy of Michael Michael Kors
Michael Michael Kors michaelkors.com
$185.00

These chunky-heeled combat boots are the perfect pairing for your fall floral dresses.

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Snake-Print Leather Pull-On Hiking Boots
Courtesy of Aquatalia
Aquatalia saksfifthavenue.com
$550.00

Heavy-duty enough for hiking, these snake print ankle boots will also look right at home on city streets.

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Miller Wool Lug Sole Boot
Courtesy of Tory Burch
Tory Burch toryburch.com
$224.25

These lug-sole boots are the perfect companion to an autumnal wardrobe brimming with fabrics like corduroy and tweed.

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Alps Boot
Courtesy of Brother Vellies
Brother Vellies brothervellies.com
$795.00

Invest in these for fall, and you're sure to wear them on repeat throughout the winter season.

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Cosmo 2.0 Chelsea Boot
Vagabond Shoemakers nordstrom.com
$194.95

The work boot is one of fall's most sought-after shoes this season, so when you find a pair you love online, start punching in your credit card number. My pick is this chunky platform boot with a bit of a punk-rock attitude. 

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Magnetic Calf Boot
Courtesy
Kendall Miles kendallmilesdesigns.com
$395.00

These ankle boots feature everything, from glass studs to gold-rimmed embellishments, if you're looking for a shoe that has some extra personality. They're made in Italy and have a double padded leather insole for a comfortable, cushioned feel. 

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In The Loop Woven Boots
FP Collection freepeople.com
$168.00

I'm a yes when it comes to woven footwear, which is why I gravitated towards this bootie. It comes in two colors, so if the mustard yellow isn't for you, try the light grey. Wear socks if you wish, though I'd go without. 

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Ankara Green Bootie
dr. Liza drlizashoes.com
$595.00

You'll be able to walk miles in this bootie; dr. Liza's shoes are all equipped with a comprehensive orthotic insole, a shock-absorbing platform, and a rocker sole to alleviate metatarsal pressure to name a few. Sign me up for a pair. 

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Tabi Faux Leather Sock Booties
Courtesy of Shopbop
Maison Margiela shopbop.com
$895.00

For the ankle boot that will really draw some accolades, invest in Maison Margiela's iconic "Tabi" booties. The split-toe design makes it unlike any other shoe you've ever worn.

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Kaylee Ankle Boot
Courtesy of Vionic Shoes
Vionic Shoes vionicshoes.com
$169.95

This taupe-colored bootie has a knit upper that comfortably wraps around your ankles. The shoe is weather-resistant, so you can breathe a sigh of relief when you're wearing them and there's a light drizzle outside.

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