Unlock Equestrian Chic: The Essential Guide to Styling Riding Boots

No woman’s closet is complete without a pair of riding boots. They’re a classic piece of footwear that can instantly elevate your look and give it an equestrian twist. You don’t have to be a horse rider to appreciate the aesthetic of riding boots.

Traditional black equestrian boots paired with white breeches showcase the timeless riding uniform (Credit: WENN)

This style fundamentally differs from other shoes, like Chelsea boots or over-the-knee boots. Riding boots put some women off because they’re unsure how to style them.

Our guide tells you everything you need to know about riding boots and how to incorporate them into your daily wardrobe.

From the Saddle to the Sidewalk: The Evolution of Riding Boots

Riding boots first became popular during the 1600s when they became a standard part of military uniforms. They protected the legs while riding by preventing them from rubbing against the saddle, and were made of leather.

Their height was determined to stop the saddle from irritating the rider’s leg. This early style of riding boots had a short block heel to keep the rider’s foot inside the stirrup.

Sleek brown and black leather riding boots highlight modern equestrian elegance

You might think riding boots look similar to Wellington boots. You would be right to make the connection. The Duke of Wellington took inspiration from the riding boot to create the Wellington boot, which was first made in rubber in 1852.

Riding boots have changed little since they first appeared in the 1600s. Most styles are still made using leather, and the original shape remains. Your riding boots today will be more comfortable, incorporating the latest footwear innovation.

Riding boots tend to have a low heel, although you will find styles that offer a higher heel. While leather is still the most common material, you can often find vegan leather alternatives and vinyl options.

Riders stride confidently in classic black field boots designed for both form and function (Credit: WENN)

These shoes have transcended from an equestrian shoe to the ultimate fashion staple while staying true to their heritage. Almost every brand will offer at least one style of riding boots in its permanent collection.

These boots are a go-to shoe for when the temperature drops and you want to bundle up against the cold. Riding boots will forever be associated with their equestrian heritage and have become synonymous with classic English style.

What Makes Riding Boots Unique: Key Design Differences

The first thing that distinguishes riding boots from regular boots in your closet is their height. You likely wear a short boot, most likely at ankle height.

Riding boots reach just below your knee, giving you mobility while covering your calves. Depending on your height, a pair of riding boots should go a few centimeters below your knee. You can also find shorter options that sit just above your mid-calf.

Comparing ankle and knee-high brown leather boots reveals how shaft height changes the silhouette

The sole of a riding boot is different than your regular boots. These shoes are designed with a textured sole to make walking easier. You’ll rarely see a pair of riding boots with a heel higher than 2 or 3 inches, whereas other boot styles can incorporate a stiletto heel.

The rear view shows detailing and closures that distinguish short heeled boots from tall riding styles

While most boots are pull-on shoes, riding boots tend to incorporate a full-side zipper. This feature makes it easier to wear the boots over jeans or, traditionally, with fitted leggings for horse riding.

How to Wear Riding Boots: Outfit Ideas for Every Occasion

Riding boots are casual shoes that look more elevated than sneakers and give you a polished look without wearing heels. You can think of them as a way to bring comfort to your outfit without compromising style.

The easiest way to style riding boots is with your favorite jeans. Channel your inner equestrian with a blouse and a leather belt.

Athina Onassis de Miranda defines equestrian elegance: the iconic polo, pants, belt, and riding boots ensemble (Credit: WENN)

Riding boots are essential for anyone who wants to encapsulate the New England preppy style synonymous with American brands, such as Ralph Lauren. You can wear this winter-appropriate outfit with a knitted sweater over your blouse.

Fashion icons Claudia Schiffer and Gwen Stefani showcase chic ways to style riding boots — from cozy knits to sleek monochrome looks (Credit: WENN)

You can wear riding boots to work if your office culture allows for jeans. Adding a fitted blazer or a silk blouse can give your outfit a more professional feel.

Leather riding boots are more appropriate for the office than vinyl alternatives, and it’s best to choose a pair with a patent finish.

Irina Shayk, Kourtney Kardashian, and Amy Adams prove that knee-high riding boots paired with tailored blazers create polished, versatile street style (Credit: WENN)

You can pair your jeans and riding boots with a color-block tunic top for an off-the-clock look. Anything you wear with jeans is almost sure to work with riding boots.

Don’t get trapped with the idea that you can only wear riding boots with jeans. It’ll largely depend on the finish of your shoes and your style.

If you have a pair of classic riding boots in a leather finish, you can wear them with tights and a fit-and-flare dress. This outfit is an excellent go-to for transitional months when you want to wear a dress but don’t want your legs to get cold.

Kris Jenner, Pippa Middleton, and Blake Lively each bring winter sophistication to riding boots with tailored coats and dark tights (Credit: WENN)

Sweater dresses perfectly combine with riding boots, making the outfits a winter staple for your wardrobe.

Ashley Roberts, Frankie Bridge, and Taylor Momsen reinterpret sweater-dress styling with knee-high and over-the-knee boots for a modern cold-weather edge (Credit: WENN)

When to Swap Riding Boots for Shorter Styles

While riding boots are versatile, there are a few occasions where a shorter boot is more appropriate. In most cases, you replace a pair of riding boots with a shorter style, like combat boots.

However, there will be times when boots won’t be appropriate for where you are going.

Wearing denim shorts with riding boots will make your legs appear shorter and can make you look stouter. Swap out the shoes for Chelsea boots or a shorter style to elongate your legs and show off your fresh tan.

Unless you live in a climate where it’s freezing all year round, you’ll want to retire your riding boots during the summer. The style isn’t practical once the temperatures start rising, and you can quickly become uncomfortable, particularly with leather riding boots.

Swap them out for a shorter pair of ankle boots if you can’t do without wearing boots. Riding boots are not shoes for more formal occasions. If you’re heading to a bar or an upmarket restaurant, you’ll want to wear boots with a heel.

Riding boots can feel too laid-back for dressier occasions like family gatherings or birthday dinners. Think of them as your elevated alternative to sneakers or flats—perfect for casual-chic settings but best swapped out when the dress code calls for something more refined.

Are Riding Boots Still in Style? Why They’ll Always Be a Classic

If you want to get the most out of your riding boots, try choosing a pair in a versatile color. Black is classic, while brown is the perfect neutral. Consider your wardrobe and what style will be easiest to incorporate.

Anyone who loves vintage fashion will want to own a pair of riding boots. They’re a classic staple that will never go out of style. Shoe trends might ebb and flow, but you’ll never look out of date in riding boots.

Riding boots are timeless shoes with a unique heritage. They instantly remind me of their equestrian origin, and they can elevate even a jeans and a T-shirt outfit.

Riding boots are a staple in classic English fashion, whether your style icon is Princess Diana or Kate Moss. As fashion trends look to the past for inspiration, riding boots will become a must-have shoe.

These shoes are a worthwhile investment for your wardrobe and a style you’ll reach for from autumn to spring.

Explore More Equestrian & Boot-Inspired Fashion

From timeless riding silhouettes to modern reboots of classic equestrian footwear, these Your Next Shoes features highlight how celebrities and designers continue to reinterpret this enduring style. Whether you’re drawn to polished leather knee-highs or Western-inspired variations, explore more articles that celebrate the art and versatility of the riding boot.