![These Ankle Boots Are Made for Walking, and They're Super Comfortable Too (1) These Ankle Boots Are Made for Walking, and They're Super Comfortable Too (1)](https://i0.wp.com/hips.hearstapps.com/hmg-prod/images/everlane-shoe-hero-format-1667221220.png?crop=0.502xw:1.00xh;0.240xw,0&resize=640:*)
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There's something almost magical about ankle boots. They're put together without being too fussy, and the right pair can bestow a little added support and lift. Thankfully, we're seeing more thoughtful features like cushioned footbeds, arch support, soft interior lining, and sturdy soles for traction. Durable materials and a generous fit also contribute to the walkability factor. If you're looking for a little lift, don’t worry—height doesn’t mean pain anymore! Block heels are ideal for a long day of being on your feet. Comfortable heel and platform bootie styles with the aforementioned technology exist, too.
Our Top Picks
1
Best Chelsea Ankle Boots
Everlane Italian Leather Chelsea Boot
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2
Best Western Ankle Boots
Dr. Scholl's Lawless Block Heel Ankle Boots
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3
Best Ankle Boots on Amazon
Amazon Essentials Microsuede Ankle Boot
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4
Best Ankle Rain Boots
Dolce Vita Linny H2O Waterproof Boots
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9
Best Patent Leather Boots
Naturalizer Madalynn Patent Black Leather Bootie
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10
Best Clog Boots
Dansko Maria Clog Boots
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The best part? Ankle boots effortlessly pair with almost any outfit. Need something to go with your new high-waisted pants? Check. Perhaps you're more of a skirt person. Also fine. You can, of course, always style them with your favorite jeans as well. Heading into fall, you'll likely need a pair of transitional ankle boots to replace the comfortable sandals and espadrilles you've been wearing all summer. Trust us: No matter the season, we're certain you'll get a ton of wear from these most comfortable ankle boots.
1
Best Chelsea Ankle Boots
Everlane Italian Leather Chelsea Boot
1
Best Chelsea Ankle Boots
Everlane Italian Leather Chelsea Boot
You won't regret investing in these Everlane Chelsea boots. While the cushioned footbed guarantees comfort inside, the outside is made from a beautiful, supple Italian leather, and the gum sole provides traction.
You'd never guess that these stylish black ankle boots were from Dr. Scholl's, thanks to a modern Western-inspired silhouette complete with an almond toe and block heel. Inside, a memory foam footbed guarantees all day support and comfort. They also come in white, tan, and brown, as well as wide sizing.
3
Best Ankle Boots on Amazon
Amazon Essentials Microsuede Ankle Boot
3
Best Ankle Boots on Amazon
Amazon Essentials Microsuede Ankle Boot
Wear this versatile suede-like bootie, which is available in wide options, with everything from denim to floaty floral dresses. The stacked heel gives you a lift, while the padded footbed supports each step.
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4
Best Ankle Rain Boots
Dolce Vita Linny H2O Waterproof Boots
4
Best Ankle Rain Boots
Dolce Vita Linny H2O Waterproof Boots
These stylish tan suede ankle boots are fully waterproof, so you don't have to worry about unpredictable weather. They also come in five dreamy fall colors, from black leather to olive suede. Because they go to a size 13W and have wide options, the Linny H2O booties are also a smart choice for larger or wide feet.
5
Best for Arch Support
Vionic Shantelle Gray Suede Ankle Bootie
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Best for Arch Support
Vionic Shantelle Gray Suede Ankle Bootie
Don't let the sleek style fool you: These block heel ankle booties are waterproof and have a grippy rubber sole for added traction. A removable EVA insole provides all-day arch support.
We predict this pull-on style in worn-in brown leather will be your go-to for casual looks. The stacked heel gives you a slight lift, and the lightly cushioned insole provides relief.
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Best Chunky Sole Ankle Boots
Marc Fisher Padmia Lug Sole Chelsea Boot
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Best Chunky Sole Ankle Boots
Marc Fisher Padmia Lug Sole Chelsea Boot
From the pull-on style to the platform grip lug sole, these suede Chelsea boots offer thoughtful details. Did we mention that they're seriously marked down right now?
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Nothing screams comfort like slipping your cold toes into the furry interior of an Ugg boot, and ah, you feel like you're walking on clouds. Perhaps they're not your go-to office shoe, but if all you are after is comfortable ankle boots, then these are the winners.
14
Best Zipper Fastened Ankle Boots
Vince Women's Hilda Black Leather Ankle Boots
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Best Zipper Fastened Ankle Boots
Vince Women's Hilda Black Leather Ankle Boots
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If you're looking for a comfortable heeled bootie, these gorgeous Vince shoes come above the ankle and have a modern small heel for stability. It's just the right amount of lift to support your arches.
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Best Square-Toe Angle Boots
Maguire Mora Black Leather Chelsea Boot
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Best Square-Toe Angle Boots
Maguire Mora Black Leather Chelsea Boot
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Maguire's square-toe silhouette gives a modern touch to these otherwise timeless classic Chelsea boots. They make a fabulous everyday style, and also come in brown or white leather. We also like that you can slip in and out of them.
Sara Klausing
Sara Klausing covers all things fashion and style for Oprah Daily. Follow her on Instagram.