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 height, sole construction, and bevy of embellishments for just about any fashion play. So consider investing in a pair (or two) of ankle boots that you can test-drive now and live in year-round. We’ve hand-picked our favorites.
Aldo Reflow Combat Ankle Boot
These fatigue green boots come with a knitted upper that wraps comfortably and snuggly at the ankles to keep out the cold.
Dr. Martens Brown Faux-Fur Jadon Platform Boots
Get cozy in this platform and faux-fur trimmed pair of classic Dr. Martens.
Freda Salvador Ace Lace Up Boot
Take a closer look at these black combat boots, and you’ll notice the sweet eyelet detailing.
Ann Taylor Zebra Print Haircalf Blade Heel Booties
In place of leopard print, embrace a bolder zebra motif this season.
Totême The Ankle Leather Chelsea Boots
Your everyday black Chelsea boot just got a minimalist update.
Michael Michael Kors Dupree Leather Platform Booties
Hefty lug sole boots dominate this season, making this pair a must-have for minimalist tastes.
Staud Lars Leather Boots
These pointed ivory boots are the perfect to pair with loose trousers and dresses.
Tory Burch Jessa Lug-Sole Ankle Boot
Not all ankle boots are equal, like these lug-sole leather boots decorated with statement gold hardware.
Rag & Bone Axel Mid Booties
Say hello to the perfect everyday suede ankle boot.
By Far Kah Stretch-Suede Ankle Boots
Tough for the elements, but sleek and flexible for modern everyday style.
We The Free Wesley Ankle Boots
Live your best Western life in these ankle-length cowboy boots.
Chelsea Paris Tux Loafer Boot
Patent leather and a gunmetal finished metal plate dress up these formalwear-inspired ankle boots.
Porte & Paire Leather and Ribbed-Knit Ankle Boots
Ribbed knit detailing brings an element of coziness to these lug-sole boots.
Kendall Miles Magnetic Boot
If you’re looking for an ankle boot with extra personality, this pair features attention-grabbing glass studs and gold-rimmed embellishments.
Gia Borghini Marte Leather Ankle Boots
Chunky rubber soles are the look of the moment—offset this pair with a flowing midi dress.
Loeffler Randall Bridget Black Chelsea Combat Boot
Slip into these stretch-knit ankle boots that will look equally polished with a dress or cropped jeans.
Ugg Classic Sugar Ultra Mini
Throw it back to the '00s with UGGs' Ultra Classic mini bootie.
Dr. Liza Lavender Bootie
We give these lavender ankle boots an emphatic “yes!” for spring. Bonus: They're equipped with a shock-absorbing platform and rocker sole to alleviate metatarsal pressure.
Moncler Helis Leather Hiking Boots
Heavy-duty enough for hiking, these glittering ankle boots will look right at home on city streets.
Schutz Mikki Booties
This ivory ankle boot is ultra-sleek for dressier moments.
Vagabond Shoemakers Cosmo 2.0 Chelsea Boot
The work boot is one of fall’s most sought-after shoes. We love the chunky platform on this pair for a bit of a punk-rock attitude.
Proenza Schouler Lug-Sole Leather Chelsea Boots
Trade out your overly worn brown ankle boots for this rugged yet refined pair by Proenza Schouler.
Sorel Brex Heel Lace Bootie
Practicality and style combine in these heeled lace-up hiker rain boots.
Moon Boots Shearling and Suede Snow Boots
Moon Boot’s shearling ankle-length snow boots are the It après-ski style of the season.
Cougar Firenze Gloss Waterproof Chelsea Boots
These glossy ankle boots will take on puddles and wet fall leaves with ease.
Brother Vellies Alps Boot
Invest in these for fall, and you’re sure to wear them on repeat throughout the winter season.
The Row Boris Leather Ankle Boots
The ultimate pared-back ankle boot for luxury lovers.
Maison Margiela Tabi Sock Boots
Maison Margiela’s iconic “Tabi” booties with a split-toe design are the ankle boots guaranteed to turn heads.
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Bring it on, cold weather.
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