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Womens/Shoes/Boots/Ankle Booties & Tall Boots

Top 10 Riding Boots

The Most Comfortable Riding Boots For Everyday Wear—According To Shopping Data

Image credits: colehaan

When the temperatures start to drop, there’s only one thing we want to think about: boots. Indisputably one of the best parts of winter fashion, boots come in all shapes, sizes, and colors, from ankle-high, heeled booties to the always-reliable riding boots.

Speaking of riding boots, they seem to be one of the few boot trends that have outlasted the fad phase, becoming a classic silhouette with closet-staple status. More laidback than those of the thigh-high, high-heeled variety, riding boots boast comfort and versatility ideal for everyday wear. You can pair them with a chunky sweater dress or wear them with jeans and a turtleneck—either way, you’re going to look chic and feel comfortable. 

Plus, there’s a pair of women’s riding boots out there for every kind of wardrobe, from refined equestrian vibes to rugged Western styles. And guess what? We went to work to find the best riding boot styles on the internet so that you can skip the research phase and get straight to shopping.

How We Found The Best Riding Boots

If you’re new here, we’ll give you the lowdown: our Top 10 lists are built with the help of our ranking algorithm, a tool that scores products based on information from social media, reviews, and industry news. Then, we take the top-rated picks in a given category and compile our lists, making sure to provide you with everything you need to know (for example, if a style tends to run small) to make the most-informed purchase decision possible. So, ready to see which riding boots were endorsed by our data-powered algorithm? All that’s left to do is scroll down.

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January 22, 2024

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

Kenneth Cole Leanna Knee High Boot

Overall Score

4.25

10

Kenneth Cole Leanna Knee High Boot

4.1

38 User Reviews

2.3

Best Seller

3

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 Low Block-Heel Riding Boots

DEFINING DETAILS
If you're someone who struggles finding a boot that fits your calves well, look no further than the Leanna Knee High Boot from Kenneth Cole. The stretch panel on the shaft hugs your claves to give you the perfect snug fit. 

WHAT ELSE TO KNOW
These boots combine leather and fabric details for a stylish flare. 

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Cole Haan Noelle Boot

Overall Score

4.35

09

Cole Haan Noelle Boot

4.2

345 User Reviews

2.8

Best Seller

3

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.

Best Riding Boots With Flexible Shaft

DEFINING DETAILS
From the soft leather construction and stretch back panel to the luxuriously cushioned footbed, Cole Haan's Noelle Boot boasts extreme comfort, flexibility, and daylong support. 

WHAT ELSE TO KNOW
Snag these boots in three colors: Black, Chestnut, and Tornado. 

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Sam Edelman Mable Riding Boot

Overall Score

4.4

08

Sam Edelman Mable Riding Boot

4.13

81 User Reviews

2.5

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.

Best Rounded-Toe Riding Boots

DEFINING DETAILS
A classic take on the riding silhouette, Sam Edelman's Mable Riding Boot is bound to get a lot of wear just for the simple fact that its sleek, high-quality leather design pairs well with just about anything in your closet. 

WHAT ELSE TO KNOW
It comes in two rich shades: Rich Cognac Leather and Spiced Pecan Leather. 

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INC International Concepts Fawne Riding Leather Boots

Overall Score

4.4

07

INC International Concepts Fawne Riding Leather Boots

4

1215 User Reviews

3.1

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 Riding Boots With Flexible Shaft

DEFINING DETAILS
While the appearance of these leather riding boots is undeniably stunning, what’s really special is what’s inside: a handmade sole. That level of craftsmanship can’t be undervalued in a pair of boots, which is why you might want to purchase these in multiple colors.

WHAT ELSE TO KNOW
Good news: there’s a wide calf version. 

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Frye Melissa Button Knee High Boot

Overall Score

4.4

06

Frye Melissa Button Knee High Boot

4.06

3319 User Reviews

3.3

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 Western Riding Boots

DEFINING DETAILS
If “rustic” is an adjective you’re drawn to, we’ve got the boots for you. With a burnished leather upper and a plain toe box, these brown riding boots from Frye could easily be worn to ride off into the sunset. 

WHAT ELSE TO KNOW
There are two subtle design details worth noting on the Melissa Button 2 boots: first, the antique logo hardware at the top, and second, the embossed “F” just above the block heel. 

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Lifestride Xtrovert Riding Boot

Overall Score

4.4

05

Lifestride Xtrovert Riding Boot

4.7

4 User Reviews

2.1

Best Seller

3

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.

Best Cushioned Riding Boots

DEFINING DETAILS
Designed with a low stacked heel and cushioned footbed, the Lifestride Xtrovert Riding Boot was made with your comfort in mind. It's also made with a Velocity 2.0 insole that features shock absorption and pressure distribution to bring even more support to each step.  

REVIEW HIGHLIGHT
“I have been searching for new brown boots for a few months now. Having a size 11 foot comes with issues sometimes in finding the right fit. These boots are the perfect fit! I wore them for a whole day the first time wearing them my feet were comfortable the whole time. I wore thinner socks and am hoping as the leather stretches I can move to slightly thicker socks but am very happy with these boots."

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Naturalizer Rena Boot

Overall Score

4.45

04

Naturalizer Rena Boot

4.26

842 User Reviews

3

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.

Best Riding Boots For Narrow And Wide Calves

DEFINING DETAILS
The Naturalizer Rena Boot represents everything we love about a timeless riding boot. Marked by its fashionable appeal and functional nature, this riding boot neither compromises on comfort or style thanks to its almond toe silhouette, smooth leather, and wraparound straps.

WHAT ELSE TO KNOW
Like all Naturalizer shoes, the Rena boot is made with with Contour+ technology to make walking and standing more comfortable. You can also snag these in Black, Cider, or Chocoloate shades and in wide calf or narrow calf size options. 

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Banana Republic Cheval Leather Riding Boot

Overall Score

4.5

03

Banana Republic Cheval Leather Riding Boot

4

48 User Reviews

5

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.

Best Leather Riding Boots

DEFINING DETAILS
At almost $600, Banana Republic’s Cheval Leather Riding Boots are definitely a splurge. But they have a lot going for them; for example, they’re crafted from a sturdy, bonded leather that softens and molds to your feet with every wear.

REVIEW HIGHLIGHT
“These boots are impeccably constructed out of the most beautiful footwear leather. They are true to size and easy to slip on, but note that the calf circumference is narrow and best fits a slender-to-average leg. I am 6 ft tall and 142 lbs. I wear a size 10.5 shoe and these boots fit perfectly. For me, they are well worth the price, which I find to be competitive with other brands of quality leather boots.”

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Dream Pairs Wide Calf Riding Boots

Overall Score

4.6

02

Dream Pairs Wide Calf Riding Boots

4.4

18547 User Reviews

5

Best Seller

3

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.

Best Affordable Riding Boots

DEFINING DETAILS
When the word “comfortable” is part of a product’s name, we’re in. Especially considering these women’s riding boots are fashionable and affordable too. Not to mention, they come in over 30 different colors. 

WHAT ELSE TO KNOW
Wide calves and riding boots aren't always a harmonious pairing, but Dream Pairs is trying to change that. They designed this style to fit wider than regular sizes, and they even included adjustable side buckles and inset zippers for easy on and off. 

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Sam Edelman Penny Boot

Overall Score

4.8

01

Sam Edelman Penny Boot

4.24

6893 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 Riding Boots Overall

DEFINING DETAILS
The distressed coin button details, super-soft imported leather exterior, and asymmetrical shaft are what make these riding boots the best of their kind. And because they’re made to look worn-in, no one will know they’re a recent addition to your wardrobe. 

WHAT ELSE TO KNOW
You can purchase Sam Edelman’s Penny Riding Boots in black, burnt brandy, and whiskey. Plus, you can choose from regular and wide calf sizes for the most comfortable fit possible. 

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