Top 10 Riding Boots
The Most Comfortable Riding Boots For Everyday Wear—According To Shopping Data

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 and became 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.
December 19, 2022
Written By:Sierra Rogers
Product Expert:Georgia Jones
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
Naturalizer Kalona Riding Boot
Overall Score
4.2
10
Naturalizer Kalona Riding Boot
4.49
45 User Reviews
2.4
Best Seller
0
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 Heeled
DEFINING DETAILS
Naturalizer is a recognized name in the business of leather goods, and their Kalona Riding Boots are just one example of why. With a sleek buckle and an almond-shaped toe box, these tall riding boots are the epitome of sophistication.
WHAT ELSE TO KNOW
In addition to the classic black color, these riding boots are available in a dark brown leather version. Also, you can choose between medium or wide width for added comfort.
More Colors
Lucky Brand Inifita Riding Boot
Overall Score
4.25
09
Lucky Brand Inifita Riding Boot
4.7
24 User Reviews
2.3
Best Seller
0
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 Cushion
DEFINING DETAILS
Inspired by classic equestrian boots, Lucky Brand’s Inifita Riding Boots are made to last for seasons to come. They have a padded footbed, elastic gore insets for comfort, a block heel, and buckle accents for style.
REVIEW HIGHLIGHT
Here’s a review for these boots that was written less than a month ago: “I just bought these boots. Wore them right away and LOVED them! Favorite boot ever. Good height. Great width in the foot and at the calve. Super comfortable! Fit true to size. Purchased black and may go back and buy brown too!”
More Colors
Dream Pairs Wide Calf Riding Boots
Overall Score
4.3
08
Dream Pairs Wide Calf Riding Boots
4.4
8435 User Reviews
3
Best Seller
0
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 For Wide Calves
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.
More Colors
Frye Paige Tall Riding Boot
Overall Score
4.35
07
Frye Paige Tall Riding Boot
4.21
793 User Reviews
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.
Best Vintage
DEFINING DETAILS
Another notable name in leather goods, Frye’s craftsmanship shines in the Paige Tall Riding Boots. Made with vintage Italian leather, this style has a square toe, a low block heel, and functional pull tabs.
CARE TIP
To keep your leather riding boots in prime condition, consider investing in a weatherproof balm. Usually applied directly to the exterior of your shoes, weatherproof balms help protect leather from damage caused by rain, snow, and dirt.
More Colors
Vince Carleigh Riding Boots
Overall Score
4.4
06
Vince Carleigh Riding Boots
4.3
3 User Reviews
2.1
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 Luxury
DEFINING DETAILS
Sleek as can be, Vince’s Women's Carleigh Riding Boots feature a clean, frills-free silhouette made entirely out of imported leather.
WHAT ELSE TO KNOW
Due to their rubber sole, these boots can take on a puddle or two—just don’t forget to treat them with a weatherproof balm beforehand.
Banana Republic Cheval Leather Riding Boot
Overall Score
4.4
05
Banana Republic Cheval Leather Riding Boot
4.7
3 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 Flat
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.”
More Colors
Frye Melissa Button Knee High Boot
Overall Score
4.45
04
Frye Melissa Button Knee High Boot
3.99
1452 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 Western
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.
Sam Edelman Drina Riding Boot
Overall Score
4.5
03
Sam Edelman Drina Riding Boot
4.37
16 User Reviews
2.2
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 Square Toe
DEFINING DETAILS
Designed to elongate the appearance of your legs, these tall riding boots from Sam Edelman feature a square toe box and a walkable block heel.
REVIEW HIGHLIGHT
“I just got the Drina boot in and they’re gorgeous! The material is strong, smooth, and very comfortable on my leg. They hug so nicely, a perfect fit! I was originally going to get the Penny boot, but I’m glad I decided on the square toe instead since it’s a bit “cooler” in style. They will definitely be a go-to in my closet!”
More Colors
INC International Concepts Fawne Riding Leather Boots
Overall Score
4.5
02
INC International Concepts Fawne Riding Leather Boots
3.9
568 User Reviews
4
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 For Smaller Calves
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.
More Colors
Sam Edelman Penny Boot
Overall Score
4.95
01
Sam Edelman Penny Boot
4.24
6713 User Reviews
5
Best Seller
5
Industry Recognition
5
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 Overall
DEFINING DETAILS
The distressed coin button details, super-soft imported leather exterior, and asymmetrical shaft are what makes 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.
More Colors
The Latest
From Our Partners