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The 30 Best Ankle Boots for Women to Wear This Winter

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Boot season is officially here, and while there are a variety of women’s boots out there, the best ankle boots top shoppers lists year after year. After all, they’re a timeless style you won’t get sick of wearing.

The Different Types of Ankle Boots

Ankle boots can range in design, but they’re described as a boot that covers the whole foot up to the ankle.

  • Chelsea Boots: an iconic type of ankle boot with a close-fitting elastic side panel.
  • Hiking Boots: specifically designed for protecting the feet during outdoor activities.
  • Combat Boots: a classic lace-up style that usually hits right above the ankle.
  • Platform Boots: characterized by a chunky, usually flat, sole that typically adds a few inches of height.
  • Heeled Boot: can range from thick block-heeled to stilettoed styles for lift.
  • Cowboy or Western Boots: traditionally detailed with western elements like stitching, a snip toe design and no lacing.
  • Winter Boots: cold-weather boots intended to keep feet warm and protected, usually insulated and fully lined with a cozy material.
  • Rain Boots: a waterproof boot typically made of rubber or plastic.

How to Find the Most Comfortable Ankle Boots for Women

When searching for your perfect pair, comfort is a key factor to consider, notes Dr. Jackie Sutera, Vionic Innovation Lab Member and New York-based podiatrist. “As a starting point, look for boots that have a cushioned insole with arch support,” she says. “This provides comfort and shock absorption. Also, look for a stacked or a low heel for everyday use. Avoid very flat, or platform heeled boots as your go-to boots.”

And if you have common foot issues like bunions or hammertoes, Dr. Sutera also advises looking for options with some key features. “People with bunions, wide feet and/or hammertoes should look for styles that can accommodate the forefoot, like materials made of a mesh or a soft, forgiving leather,” she says. “These folks should also avoid toe boxes that are tight, narrow, and pointy.”

For people who suffer from plantar fasciitis or flat feet, she suggests avoiding pairs with thin, flat insoles and outsoles.

As for plus-size women, who may have wide calves, finding affordable-yet-chic options can be a headache. But thankfully, a range of brands now offer a great selection.

With the holidays upon us, there truly is no better excuse to snag a fresh new pair of ankle boots for yourself. They’d even make a great holiday gift for someone you love (just sayin’). If you play your cards right, you might even snag a majorly discounted pair during Black Friday sales.

Below, shop 30 of the best ankle boots for women, and pick up a pair (or two) before they sell out.

Tecovas The Penny Boots

Best Western Ankle Boots

The western trend is one you should try sooner rather than later, and these authentic cowboy boots are a great way to get into it. The modern ankle bootie is crafted with genuine calfskin. Minimally embellished with a touch of contrast stitching and available in five rustic shades, these can easily be styled with a variety of looks — from slip dresses to denim on denim.

Tecovas The Penny
CREDIT: Courtesy of Tecovas


Everlane The High-Ankle Glove Boots in ReKnit

For an ultra-sleek look, try these glove-fit ankle boots that hit mid-calf. They feature 100% recycled polyester uppers, a trendy square toe and comfy stacked heel. In addition to classic black, they come in three fun fall shades: Toffee, Pale Yellow and Caper Green. The holiday-favorite style looks sophisticated when paired with flirty dresses and trousers.

Everlane The High-Ankle Glove Boot in ReKnit
CREDIT: Courtesy of Everlane


Dr. Martens Jadon Boots

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Best Combat Boots

Haven’t you heard? Dr. Martens are officially back. The iconic ‘90s trend is making the Instagram rounds, and for good reason. The shoes’ clunky soles will add a punk rock touch to a floral mini dress or jeans and tee combo. For just under $200, these are bound to be heavy in your rotation.

Dr. Martens Jadon Boot
CREDIT: Courtesy of Dr. Martens

 


Ugg Adirondack III Boots

Best Winter Boots for Women

Ugg’s Adirondack III is the total package. Not only are these cute winter boots, but they’re also super easy to slip on and off and provide neutral arch support for optimal foot health. With a super cozy fleece liner and waterproof leather outer, they’ll keep your feet warm and dry in frigid climates. And the liner is insulating, featuring 200 grams of wool for toasty effects at any temperature.

Ugg Adirondack III
CREDIT: Courtesy of Amazon


Christian Louboutin Marchacroche Boots

Best Leather Ankle Boots

Classic black ankle boots will never do you wrong, so you’re smart to want to invest in a designer pair. Christian Louboutin may be known for its red-bottom heels, but these everyday boots from the brand also earn high marks. They’re made of super-soft Italian calfskin leather and feature a round-toe silhouette for an easy pairing  with your winter favorites. Think: big coats, leather leggings, mom jeans and more.

Christian Louboutin Marchacroche Boots
CREDIT: Courtesy of MyTheresa


Isabel Marant Crisi Ankle Boots

Also Consider Western Ankle Boots

The western vibe strikes again, this time with a softer silhouette. These concealed wedge booties are lined with leather and feature an outer suede layer. Brought to you by French designer Isabel Marant, these are effortlessly chic. Wear them with bare legs, if you dare, or pair them with jeans and a sweater for a classic winter look.

Isabel Marant Crisi Ankle Boots
CREDIT: Courtesy of MyTheresa


The Row Zipped 1 Leather Ankle Boots

There’s no cooler way to rock the platform boot trend than with this luxurious pair from The Row. Crafted in Italy, the chunky style is dressed in calfskin leather from the inside out and adorned with a utilitarian-style front center zipper. Pair these with any minimalist look like head-to-toe black or neutrals.

The Row Zipped 1 leather ankle boots
CREDIT: Courtesy of MyTheresa


Koio Chelsea Boots

Best Chelsea Boots

The smooth leather boots are easy to slip on and off, thanks to the elastic side panels and a heel tab. The clunky lug soles are surprisingly lightweight and the entire shoe is water-resistant. They’ll elevate any look, from casual legging combos to a maxi dress and leather jacket.

Koio Chelsea
CREDIT: Courtesy of Koio


Chooka Plush Chelsea Boots

Best Ankle Rain Boots

On rainy days, opt for these lined Chelsea-style rain boots. The plush interior is an ultra-cozy complement to thick socks and is accompanied by a moisture-absorbing lining to keep feet dry and cool. The tread on these boots not only offers grip, but is also self-cleaning, meaning you don’t have to scrub at it to remove caked-on dirt and grime. A sleek matte finish gives these waterproof rubber boots a modern edge.

 

Chooka Plush Chelsea Boot
CREDIT: Courtesy of Amazon


L.L. Bean 8-Inch Bean Boots

Best Duck Boots

Featuring a hand-sewn triple stitch that keeps mud and snow at bay, the Bean boot is hands down L.L. Bean’s most iconic style. Equal parts functional and stylish, it can easily be dressed up with some mom jeans and oversized sweaters.

L.L. Bean 8-Inch Bean Boot
CREDIT: Courtesy of Nordstrom


J.Crew Winter Duck Boots

Also Consider Duck Boots

These adorable winter boots have been one of J. Crew’s customer favorites since 2017. The winter-ready style now comes updated in a pecan-hued leather with sherpa lining and a waterproof sole. Slippery pavements or snowy pathways are no match for these tough boots.

J.Crew Winter Duck Boots
CREDIT: Courtesy of J.Crew


Rocket Dog Soundoff Boot

Best Ankle Boot for Wide Calves & Feet

This everyday brown boot from Rocket Dog is a great buy for the money. Thanks to its wide opening and what customers call a roomy fit, the boot is even great for people with wide feet or calves. Their soles come in the perfect shade of brown (not too light or too dark), making them easy to style for day or night. As we transition into autumn, pair them with something form-fitting like skinny jeans or leggings to balance out the relaxed fit.

Rocket Dog Soundoff Boot
CREDIT: Courtesy of Amazon


Jeossy Ankle Boots 

Best Low-Heeled Boots

This Amazon favorite is a great casual black boot, featuring a vegan leather upper and side zipper for easy entry. The classic ankle design paired with the barely-there heel make it a perfect pick for your next business trip or weekend outing.

Jeossy Ankle Boots 
CREDIT: Courtesy of Amazon


Steve Madden Howler Booties

Best Trendy Ankle Boots

According to fall ’21 runways, this season is all about cool-girl boots with a classic thick sole and fresh feminine edge. Go for a pair done in a light pink or sand color like this style from Steve Madden. Not only will it instantly brighten up any look, but it will also pair well closet staples you’re already wearing like mini dresses, mom jeans and skinny jeans. The style’s elastic sock band forms to your ankle, which reviewers say make these some of the comfiest boots you can own.

Steve Madden Howler Bootie
CREDIT: Courtesy of Nordstrom


Dr. Scholl’s Mania Boots

Best Wedged Ankle Boots

A wedge bootie is an excellent option if you want a little height but aren’t willing to commit to a traditional heel. These lightweight, flexible slip-ons comes in two neutral shades: brown and black. So take your pick and don’t be surprised if they become your new favorite.

Dr. Scholl's Mania Boot
CREDIT: Courtesy of DSW


Marc Fisher Raila Booties

Best Snakeskin Ankle Boots

One easy way to dress up a basic outfit is to add in an animal print boot. This snakeskin pair will instantly add a sophisticated touch to jeans and a button-up for your next meeting or with an LBD for date night.

Marc Fisher Raila Bootie
CREDIT: Courtesy of DSW


Dolce Vita Huey Booties

Most Versatile Ankle Boots

Complete with a chunky rubber sole and croc-embossed upper, these versatile booties are elevated but not too fancy. They pair best with ankle-cut jeans that stop right at the top of the boot so you can see the full look. Add a silk top for a night out or a printed shirt for a weekend brunch.

Dolce Vita Huey Booties
CREDIT: Courtesy of Dolce Vita


Timberland Courmayeur Valley Water Resistant Hiking Boots

Best Hiking Boots

Equal parts rugged and stylish, these must-have Timberland hiking boots are made with a sturdy sole, cushioned footbed and a water-resistant finish. We won’t blame you if you wear them off the trail, too.

Timberland Courmayeur Valley Water Resistant Hiking Boot
CREDIT: Courtesy of Nordstrom


Chinese Laundry Finn Ankle Boots

Best Pointed-Toe Boots

An exaggerated pointed-toe bootie will add a little je ne sais quoi to your OOTD. French girls are known for that effortlessly thrown-together look which, more often than not, includes an ankle boot like this one from Chinese Laundry. It comes in five wear-with-everything colorways and one standout print.

Chinese Laundry Finn Ankle Boot
CREDIT: Courtesy of Amazon


Universal Thread Parker Combat Boots

Just because the weather is gloomy doesn’t mean your outfit has to be. Upgrade your chilly weather look by subbing in these crisp cream-colored boots. The monochromatic look is very of-the-moment, and comes complete with lace-up detailing and button-like accents for security.

Universal Thread Parker Combat Boots 
CREDIT: Courtesy of Target


A New Day Itzel Chelsea Boots

A chic Chelsea-style boot will always be a smart choice. You won’t be led astray with this Target find priced at just $39. The classic style has a comfy 2.5-inch block heel, a back zipper closure and a memory foam sole for comfort and easy wear. The bone shade is a nice departure from a go-to black options and is neutral enough to team with all your winter staples.

A New Day Itzel Chelsea Boots 
CREDIT: Courtesy of Target


Coach Lorimer Booties

This new design from Coach is on the pricier side, but with fashion-forward details like gold hardware and a double stitched design, you can’t go wrong.

Coach Lorimer Bootie
CREDIT: Courtesy of Coach


Chloé Susanna Studded Leather Ankle Boots

Best Embellished Ankle Boots

By now, you already know that ankle boots are a staple. If you’re going to pull the trigger on a designer pair, this black leather studded pair from Chloé is an excellent choice. A-listers like Miranda Kerr and Heidi Klum both own the style — need we say more?

Chloé Susanna Studded Leather Ankle Boots
CREDIT: Courtesy of Net-a-Porter


Sam Edelman Nina Combat Boots

Best All-White Ankle Boots

A bright white boot always adds an unexpected pop of freshness to your look. These synthetic leather lace-ups are more understated than your usual heavy combat boots thanks to a thin, lightweight sole. Dress them up with a cocktail dress or pare them down with your favorite casual denim pieces.

Sam Edelman Nina Combat Boot
CREDIT: Courtesy of Sam Edelman


Free People New Frontier Western Boots

Also Consider Western Ankle Boots

Lean into the cowgirl trend without veering into cheesy costume territory with this western-style option from Free People. Subtle appliqué details and a flattering slim fit ensure these will blend seamlessly into your closet. Casually tuck your baggy jeans into them or pair the boots with a flouncy skirt instead.

Free People New Frontier Western Boot
CREDIT: Courtesy of Free People


Vagabond Shoemakers Dioon Bootie

Best Platform Ankle Boot

For those of you that gravitate towards a black boot with a rounded toe, this is your classic boot with modern edge. The lugged platform sole is rugged and will lend you extra height.

Vagabond Shoemakers Dioon Bootie
CREDIT: Courtesy of Nordstrom


Naturalizer Val Boots

Best Cold-Weather Ankle Boots

Forget about sacrificing performance for style when it comes to winter boots. This pair from Naturalizer offers the best of both worlds. Trimmed with faux fur and packed with heat-retention technology, the boots are a no-brainer for surviving the harshest of weather. And, they look great with leggings, jeans and even your snow pants for après ski activities.

Naturalizer Val Boot
CREDIT: Courtesy of Nordstrom


Ugg Classic Ultra Mini Shearling Booties

Best Casual Ankle Boots

Love them or hate them, Uggs are here to stay. Luckily, you can get away with wearing the slipper hybrids outside these days. For in-between temperatures, you’ll want these cozy low-cut Uggs in your arsenal. Wear them with leggings on your way to yoga or joggers on a lazy Sunday.

Ugg Classic Ultra Mini Shearling Bootie
CREDIT: Courtesy of Saks Fifth Avenue


Sorel Harlow Rain Boots

Best Waterproof Ankle Boots

If you live in a climate where rain is a regular occurrence, weatherproof boots are a must. These side-zip ankle booties are made with moisture-wicking, full-grain leather to withstand the elements and a molded-rubber outsole to keep feet dry. An included memory-fit footbed is also supportive for walking long distances.

Sorel Harlow Rain Boot
CREDIT: Courtesy of Amazon


Journee Collection Gwenn Booties

Best Leopard Print Boots

Leopard print anything is always in style. A cool cut-out detail at the ankle makes these boots look way more expensive than they actually are. Plus, they feature a Comfort Foam insole to fight off foot fatigue as you go about your day.

Journee Collection Gwenn Bootie
CREDIT: Courtesy of DSW


How to Style the Best Women’s Ankle Boots

No matter which silhouette you choose, ankle boots are incredibly versatile. On days when you just can’t decide what to wear, you can reach for them to add a cool-girl touch to even the most basic outfits. For example:

  • A classic black leather ankle boot continues to be a fall favorite, but any neutral-toned version also pairs with virtually anything.
  • Make a statement with a metallic boot, but be sure to keep the rest of your look neutral.
  • Ankle boots look great with skinny jeans tucked into them or peeking out from underneath wide-leg pants.
  • You can’t go wrong by pairing a classic leather ankle boot with skinny jeans and a blazer, a la Nicole Riche.
  • Split-hem pants are one of the hottest trends on this side of 2021. Follow Kendall Jenner’s lead and rock the look by teaming your pair with an equally trendy platform bootie .
  • Go dramatic and pair your ankle boots with a fancy holiday dress, dramatic fur coat and patent leather booties like Anne Hathaway.

Last but not least, don’t forget to invest in some socks. The rule of thumb is to choose something that doesn’t show (a.k.a. mid-calf, ankle or no show-socks).

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