If you’re anything like us, ankle boots are probably the hardest-working pair in your everyday wardrobe. Whether flat or heeled, they’re incredibly comfortable, easy to style, and ready for any weather. They’re a smart investment if you need a new pair—reinvented each season in new shapes and materials.

Vogue’s Favorite Ankle Boots:

The Everyday Heel
Staud Wally booties
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$395 NORDSTROM

The Under-$150 Find
Free People Easy Does It boots
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$148 FREE PEOPLE

Margaux The Inga boots
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$495 SHOPBOP

The Lace-Up
Aeyde Isa boots
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$695 NET-A-PORTER

The Platform Zip
The Row zip platform booties
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$1,490 NORDSTROM

The Classic Chelsea
Gucci Horsebit boots
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$1,320 GUCCI

The Sock Boot
Toteme Contour boots
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$910 NORDSTROM

The Suede Style
Stuart Weitzman Stassi boots
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$650 NET-A-PORTER

Luxe textures like suede and shearling look great with other fall staples—think leather and denim. We’ve also been loving the sock boot look, which elevates traditional black leather styles into something more current. Of course, you can never go wrong with the classics: Chelsea boots are always city-chic, and edgy platforms like The Row’s signature zip-front boot are ready to stomp through rain, snow, or shine.

Whether you want to shake things up this fall with a statement pair or simply invest in a new signature style, these are the best ankle boots to shop for the season ahead—plus seven ways to style them from the ankle up.

Walk a Mile
Khaite’s Nevada boot is a signature for a reason: the subtle western detailing and sculptural heel are effortlessly cool, ready to dress up or down as needed. With your favorite pair of jeans and a wool scarf coat, these boots are ready to pound the pavement.

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Coss
carf jacket
$399 COS

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Levi’s
501 ’90s jeans
$110 LEVI’S

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Mansur Gavriel
Filo tote bag
$645 NORDSTROM

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Khaite
Nevada boots
$1,680 KHAITE

Put it in Neutral
Toteme’s slim, sock-like booties pair well with a matching winter-white skirt set and a draped cropped trench. The black leather grounds the soft neutrals, giving the look visual weight.

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Burberry
Rosewin trench jacket
$1,850 BURBERRY

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Lisa Yang
Maurie sweater and Charlotta skirt set
$815 NET-A-PORTER

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Lisa Yang
Maurie sweater and Charlotta skirt set
$815 NET-A-PORTER

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Toteme
Contour boots
$910 NORDSTROM

Old Stomping Ground
Gucci’s boot-meets-loafer hybrid in deep brown suede is built for park strolls with crunchy leaves underfoot. Wear it with cozy corduroys, a heavy knit, and just a peek of white tee.

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Zara
V-neck sweater
$70 ZARA

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Banana Republic
long-sleeve T-shirt
$60 BANANA REPUBLIC

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The Row
Adler pants
$1,350 NET-A-PORTER

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Gucci
Horsebit boots
$1,320 GUCCI

Night Moves
Channel your inner early-aughts Kate Moss in suede ankle boots, a stand collar military jacket, and flat-front trousers. Miu Miu’s It bag makes a great finishing touch.

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Ralph Lauren
embellished cropped jacket
$798 RALPH LAUREN

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Frame
The Low pants
$478 NORDSTROM

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Miu Miu
Rendez-vous bag
$4,700 MIU MIU

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Proenza Schouler
Uma boots
$1,090 SHOPBOP

In Tonal Harmony
For fall’s off-duty days, pair The Row’s pointed ankle boots with crisp white denim, a plush knit, and a prim brown car coat.

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Leset
Kyoto car coat
$550 BLOOMINGDALE’S

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Loulou de Saison
Jonah sweater
$840 NET-A-PORTER

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J.Crew
x Lee vintage jeans
$198 J.CREW

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The Row
Cindy boots
$1,850 NET-A-PORTER

Tough Love
A study in contrast, Aeyde’s tough lace-up ankle boot plays well with a daintier saA tin dress. A two-tone tote and a structured gray overcoat add elegant touches that keep the look from leaning too far into grunge.

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Reiss Martina coat, $698, REISS

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Dôen Davina dress, $530, NET-A-PORTER

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Loewe Switch tote bag, $3,700, LOEWE

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Aeyde Isa boots, $695, NET-A-PORTER

Cool, Colorful, and Cozy
Cashmere balloon trousers and a poppy red jacket complement the offbeat ease of Herbert Levine’s zip-front suede boots.

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Sssstein wool-blend jacket, $1,900, NET-A-PORTER

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H&M oversized sweater, $60, H&M

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Arch4 Hayden Milano pants, $845, NET-A-PORTER

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Herbert Levine Easy Does It boots, $1,660, NET-A-PORTER

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Staud Wally booties, $395, NORDSTROM

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Jude Theresa boots, $780, NET-A-PORTER

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Emme Parsons Western Minori boots, $895, NET-A-PORTER

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Jamie Haller The Lennon boots, $895, SHOPBOP

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The Row zip platform booties, $1,490, NORDSTROM

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Margaux The Inga boots, $495, SHOPBOP

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Legres 61 boots, $720, NET-A-PORTER

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Bottega Veneta Cherry boots, $1,500, BOTTEGA VENETA

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Free People Easy Does It boots, $148, FREE PEOPLE

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Saint Laurent Venetia booties, $1,750, SAINT LAURENT

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Church’s Suzanne boots, $1,195, NET-A-PORTER

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Stuart Weitzman Stassi boots, $650, NET-A-PORTER

Frequently Asked Questions
Heres a list of FAQs about styling ankle boots for fall

1 What are ankle boots
Ankle boots are boots that stop at or just above the ankle They come in many styles like heeled flat laceup and Chelsea boots

2 Why are ankle boots so popular for fall
They keep your feet warm and dry work with almost any outfit and pair easily with jeans dresses and skirts Theyre also comfortable for everyday wear

3 What colors of ankle boots should I start with
Black and brown are the most versatile and match almost everything Tan and taupe are also great neutral choices for fall

4 Can I wear ankle boots with jeans
Yes Skinny jeans look best tucked into or stacked over the boot Straight and wideleg jeans work well cropped or rolled up just above the boot

5 How do I wear ankle boots with dresses or skirts
Pair them with midi or mini skirts and dresses Showing a little leg between the hem and the boot keeps the look balanced Add tights when it gets colder

6 Whats the difference between Chelsea boots and laceup boots
Chelsea boots have elastic side panels and slip on easily Laceup boots tie like sneakers and give a more casual or rugged look

7 How can I make my legs look longer in ankle boots
Match your boot color to your pants or tights or choose a boot with a slight heel Avoid boots that cut off right at the widest part of your calf

8 Do ankle boots work with wideleg pants
Yes but the hem matters Choose pants that end just above the boot or cover most of it A fitted or pointedtoe boot looks best under wide legs

9 Can I wear ankle boots in the rain or snow
Waterproof or waterresistant pairs work for light rain For snow and ice look for boots with good tread and treat leather boots with a protective spray

10 How do I break in new leather ankle boots
Wear them around the house for short periods first use a leather conditioner and try thick socks to stretch them slightly Avoid wearing them for long walks right away

11 What socks should I wear with ankle boots
Thin or noshow socks work with most styles In cold weather wool or thermal