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Womens/Shoes/Boots/Ankle Booties & Tall Boots
Top 10 Ankle Booties

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

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 13, 2022

Written By:Rank & Style

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
Rank & Style Approved

nordstrom

Vagabond Shoemakers Marja Cap Toe Bootie

Our Score

4.4

Best Low Heel

WHAT TO LOVE
With their pointed tonal cap toe and block heel, it’s easy to pick up on the western aesthetic of these black ankle boots. However, they’re also incredibly sleek, which is why you’ll want to wear them again and again.

ADDITIONAL DETAILS
If you want your boots to be comfortable for walking, it’s best to listen to reviewers and opt for a size up from your usual. Here’s an excerpt from one shopper: “I usually wear a 7 or 7.5 in shoes (7 being a bit tight, 7.5 being perfect). I ordered an 8 as everyone says they run small and they literally couldn't be more perfect.”


Vince Camuto Enverna Ankle Boot

Our Score

4.4

Best High Heel

WHAT TO LOVE
Vince Camuto’s stunning Enverna Ankle Boots are made with a mix of suede and patent leather so that you can infuse a little bit of luxury into your fall uniform. With a 3.5” block heel, they toe the line between formal and casual, which only contributes to their versatility.

ADDITIONAL DETAILS
You can snag these best-selling ankle boots in both black suede and patent black leather, and they’re also available in beige, slate blue, and maroon.

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Madewell The Western Ankle Boot In Leather

Our Score

4.4

Best For Walking

WHAT TO LOVE
Yeehaw! Madewell’s best-selling Western Ankle Boots are made for walking, which is great news for those of us who plan on wearing them daily. They have a stacked block heel and Madewell’s Cloudlift Lite padded insoles, which means you won’t need to account for a break-in period.

USER REVIEW
“These boots are lovely. The heel is just right (not too high, but gives a little lift). The style is perfect with the Western pointed toe. I am a 9-9.5 in Madewell shoes/sandals/boots and I ordered the 9.5 and they fit me right out of the box. I would suggest choosing the larger size if you are in between sizes, mainly because they are pointed (which I was a little worried about). The leather is smooth and soft. There are very high quality boots.”

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Marc Fisher LTD. Alva Bootie

Our Score

4.45

Best Pointed Toe

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.

ADDITIONAL DETAILS
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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Mango Heel Leather Ankle Boot

Our Score

4.5

Best Budget

WHAT TO LOVE
If you’d describe your personal style as refined and sophisticated, these black leather ankle boots are the best option for you. With subtle decorative seams and a blunt, rounded toe, there’s a chance these were inspired by Carrie-Anne Moss’s wardrobe in The Matrix.

ADDITIONAL DETAILS
These boots are a part of Mango’s Committed Collection, which means that they’re crafted from sustainably sourced leather.


Free People We The Free Wesley Ankle Boots

Our Score

4.55

Best Western

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.

ADDITIONAL 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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Dolce Vita Caster H2O Waterproof Block Heel Bootie

Our Score

4.65

Best Lug Sole

WHAT TO LOVE
For those of you that live in a city where rainy days are frequently in the forecast, there’s the Caster H2O Waterproof Block Heel Booties. Easily one the best pairs of ankle boots for walking on our list, these shoes have a lugged sole for excellent traction on slippery surfaces.

ADDITIONAL DETAILS
These boots have a solid 3.5” heel, but they offer an extra boost via their .75” high platform. They run true to size, but some reviewers mention that they feel narrow, so keep that in mind if you usually gravitate towards wide sizes.

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J.Crew Stevie Ankle Boots In Suede

Our Score

4.7

Best Kitten Heel

WHAT TO LOVE
There’s something about these boots that makes them particularly stylish, and that something is their wide kitten heel. Designed to be comfortable enough for walking, these boots are made from suede leather and have a softly pointed toe.

USER REVIEW
"I ordered my usual size 7, and they fit perfectly and are very comfortable. The heel is also very wearable. I love the slim, not bulky look of these and the zipper up the back gives them a retro feel. I have thin legs and ankles and the J Crew booties fit pretty well in the ankle area (not oversized which I hate).”

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Rag & Bone Rover Chelsea Boot

Our Score

4.75

Best Investment

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.

ADDITIONAL 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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Marc Fisher LTD. Yale Chelsea Boot

Our Score

4.85

Best 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 chelsea boots 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.

ADDITIONAL DETAILS
We mentioned it earlier, 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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