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Womens/Shoes/Boots/Ankle Booties & Tall Boots

Top 10 Ankle Boots

Top 10 Alert: The Ankle Boots That Are Trending This Season

Image credits: madewell

Sandals rule summer. Block heels rule spring. And ankle boots dominate fall. At least, they do for us, because not only do they look fantastic with plaid and denim, but they’re also the best shoe for a stroll down a sidewalk littered with crunchy leaves (especially considering most ankle boots today are made to be comfortable). 

What makes ankle boots so appealing is their ability to somehow look casual and fancy at the same time. They’re chill enough for a dentist appointment and chic enough for a five-star restaurant. They also add height but still manage to be more comfortable than the alternative you have on standby. It shouldn’t make sense, but it does, and that’s why we love them. So, if you love them too, we’ve got good news: We found 10 top-rated pairs we’re confident you’ll love.  

How We Found The Internet’s Best Ankle Boots

As we said above, come fall ankle boots are a wardrobe staple. You can wear them with jeans, dresses, leggings and a sweater, or whatever else you want—the point is they’re incredibly versatile and can class up an outfit instantly. But finding a pair that’s not going to give you blisters? That’s a tall order. For that reason, we turned to our data-driven ranking algorithm, a tool that finds and scores products in order to determine which pairs are worth their price tag. Ahead, find out which ankle boots rose to the occasion, from a Madewell classic to a Free People fan favorite. 

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October 16, 2023

Written By:Sierra Rogers

Product Expert:Georgia Jones

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Top 10 Lists serve as unbiased shopping guides to the most trusted product recommendations on the internet. Products are scored and ranked using an algorithm backed by data consumers find most valuable when making a purchase. We are reader-supported and may earn a commission when you shop through our links.

The Rankings


10
Image credits: nordstrom
Rank & Style Approved

nordstrom

Marc Fisher LTD. Alva Bootie

Overall Score

4.45

10

Marc Fisher LTD. Alva Bootie

4.41

394 User Reviews

2.8

Best Seller

4

Industry Recognition

3

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

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Best Heeled Ankle Boots

WHAT TO LOVE
Shoemaking runs in the family for Marc Fisher, which is evident in the craftsmanship behind the Alva Booties. They have a textured leather exterior, elastic accordion insets (that make them easy to pull on and off), and a ribbed outsole so that every stroll you can in them is slip-free.

GOOD TO KNOW
According to Nordstrom, these boots run small, so order a size up if you value comfort in a pair of ankle boots. Also, don’t miss the additional color options these ankle boots are available in, including army green, camel tan, and ivory. 

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Everlane The City Boot

Overall Score

4.5

09

Everlane The City Boot

4

39 User Reviews

5

Best Seller

3

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Pointed Toe Ankle Boots

WHAT TO LOVE
The City Boot is a versatile, walkable shoe that's down to take on the day with you. Featuring a trendy pointed toe on an otherwise sleek shape, these leather boots are easy to pair with wide-leg pants, jeans, dresses, and more.

MORE DETAILS
In addition to Desert Tan, these boots are available in four other neutral tones (Black, Cream, Toasted Almond Suede, and Dark Brown Suede).

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Amazon Essentials Ankle Boot

Overall Score

4.55

08

Amazon Essentials Ankle Boot

4.3

4043 User Reviews

3.3

Best Seller

4

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Ankle Boots On Amazon

WHAT TO LOVE
Affordable, comfortable, and easy to throw on with any outfit, it's easy to see why Amazon Essentials' Ankle Boots have over 2,500 5-star reviews. They're made from a leather alternative and have a padded insole that's cushioned with high-quality memory foam for maximum walkability.

PROMISING REVIEW
"These boots are so versatile, they can take any outfit from drab to fab in seconds. Whether you're going for a casual jeans-and-tee look or you're ready to rock that little black dress, these ankle boots will have your back (or should I say, your feet). They're like the chameleons of footwear, blending seamlessly into any fashion situation. But wait, there's more! These boots are like the superheroes of the shoe world because they're so easy to slip on and off. No more struggling with zippers or laces that refuse to cooperate."

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Lucky Brand Basel Bootie

Overall Score

4.6

07

Lucky Brand Basel Bootie

4.4

15098 User Reviews

3.3

Best Seller

4

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Suede Ankle Boots

WHAT TO LOVE
Lucky Brand does high-quality leather justice. Their Basel Booties are a great example of what we're talking about. Described as "perfect utilitarian style," these ankle boots have a round toe, a short (1.5") block heel, and a zipper on the side that makes them easy to pull on and off.

GOOD TO KNOW
There are fourteen versions of the Basel Bootie to choose from, with options like Gartner red leather and Javan print suede.

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Madewell The Darcy Ankle Boot

Overall Score

4.6

06

Madewell The Darcy Ankle Boot

4.03

6 User Reviews

5

Best Seller

4

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Block Heel Ankle Boots

WHAT TO LOVE
Meet your new favorite fall shoe. Madewell's Darcy Ankle Boots are a high-quality, timeless pair that are well worth their $198 price tag. From the approachable almond-shaped toe to the Cloudlift Lite padding inside, these boots are designed to be worn on repeat.

GOOD TO KNOW
According to Madewell, these boots run slightly small. Keep that in mind when determining what size would fit you best.

More Colors

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Free People We The Free Wesley Ankle Boots

Overall Score

4.6

05

Free People We The Free Wesley Ankle Boots

4.33

92 User Reviews

2.5

Best Seller

5

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Western Ankle Boots

WHAT TO LOVE
If you’ve been scanning this list looking for a truly unique pair of booties, let us introduce you to Free People’s Wesley Ankle Boots. These western-inspired ankle boots feature a square pointed toe, hand-stitched details, and side tabs that’ll make it easy to pull them on as you head out the door. 

MORE DETAILS
From sky blue to washed black, these ankle boots come in ten stunning color options, each crafted from real leather. And while the nearly $300 price tag is a little steep, there’s a reason for that; These boots are artisan-made in small batches. 

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Everlane The Glove Boot

Overall Score

4.65

04

Everlane The Glove Boot

4.7

1377 User Reviews

3.1

Best Seller

4

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Knit Ankle Boots

WHAT TO LOVE
If you live in a warmer climate, go with these fan-favorite Everlane booties. Made with stretchy knit fabric, they're extra breezy and will work well into the spring and summer months, too.

MORE DETAILS
These boots are made from renewed plastic bottles—nine, to be exact.

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Rag & Bone Rover Chelsea Boot

Overall Score

4.65

03

Rag & Bone Rover Chelsea Boot

4.23

51 User Reviews

5

Best Seller

4

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Designer Ankle Boots

WHAT TO LOVE
Is there a brand out that’s doing the New York aesthetic better than rag & bone? Let us know what you think. In the meantime, we’ll be fawning over their Rover Chelsea Boots, a perfect pair of shoes that combines functional features (like their traction-enhancing rubber outsole) with timeless style. 

MORE DETAILS
Let’s be real: $398 is a lot to pay for a pair of womens chelsea boots, but one of the best reviews we read makes the case for their value: “I was really on the fence about spending $400 on a pair of boots, but I went for it and received the most perfect and comfortable boot! The feel of the leather is so soft and doesn’t cut into my ankle when I walk. The heel height is also low, so you can be on your feet all day.”

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Dolce Vita Huey H2O Boots

Overall Score

4.7

02

Dolce Vita Huey H2O Boots

4.23

748 User Reviews

5

Best Seller

4

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Chunky Ankle Boots

WHAT TO LOVE
Rainy days are no problem for Dolce Vita's Huey H2O Boots. The chunky lug sole will lift you up and away from the splash zone of puddles, and the sock detail at the ankle provides an additional layer of support and comfort. 

PROMISING REVIEW
"I ordered these on a whim and then once I hit purchase I started to feel guilty about buying them due to budgeting purposes I tried to cancel my order, but I had to receive them first though to do so. Once I received them and put them on, I loved them (and so did my husband, who is very picky!). So happy I didn’t return them. They’re so cool and comfy, and I love they’re waterproof!"

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Marc Fisher LTD. Yale Chelsea Boot

Overall Score

4.85

01

Marc Fisher LTD. Yale Chelsea Boot

4.5

660 User Reviews

5

Best Seller

5

Industry Recognition

4

Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Best Ankle Boots Overall

WHAT TO LOVE
The pointed, steel-inforced toe of these ankle boots is what makes them instantly eye-catching. But there’s more to love, because these booties are made with super-soft calf hair and include elastic gore insets. They’re also in the running for the most comfortable ankle boots on our list, considering they have short (1.5”), walkable block heel. 

MORE DETAILS
We've mentioned it before, and we’ll double down now: Marc Fisher is a shoemaker through and through. As the son of Nine West’s founder, Jerome Fisher, Marc has been studying the craft of shoemaking for over three decades. The Yale Chelsea Boot is one of the brand’s most popular styles, having garnered over 300 5-star reviews on Nordstrom’s website alone. 

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