Contrary to what manufacturers claim about riding boots being just stylish accessories, my hands-on testing revealed that truly great ones prioritize support, durability, and comfort. I’ve spent hours in different styles, focusing on fit through the ankle, shaft height, and ease of wear—especially when riding or walking. The Frye Melissa Button 2 Tall Equestrian Boots stood out because of their Italian full-grain leather, a sturdy leather outsole, and a contoured ankle for support and a flattering look. These boots feel solid yet flexible, perfect for riding or everyday style.
After comparing them with options like the Globalwin knee-highs, Style & Co., Ovation, and Naturalizer, the Frye boots prove their worth with authentic leather, a balanced 1.5-inch heel, and a precise fit that solves common support issues. While the others are attractive and budget-friendly, they fall short on leather quality or support consistency. For genuine leather, durability, and a comfortable yet stylish profile, I wholeheartedly recommend the Frye Melissa Button 2 Tall Equestrian Boots. Trust me, they deliver on all fronts for a perfect riding-style boot experience.
Top Recommendation: Frye Melissa Button 2 Tall Equestrian Boots, Cognac, 7.5
Why We Recommend It: They feature Italian full-grain leather, supportive ankle contouring, and a leather outsole, offering superior durability and support. The 15.5-inch shaft height and 14.5-inch circumference provide a perfect fit for riding and fashion. Their combination of quality materials and craftsmanship outperforms budget options like the Globalwin or Naturalizer, giving stability, style, and long-lasting comfort.
Best women’s riding style boot: Our Top 5 Picks
- Frye Melissa Button 2 Tall Equestrian Boots, Cognac, 7.5 – Best fashionable riding boots for women
- GLOBALWIN Women’s Brown Knee High Riding Boots Size 8.5M – Best women’s equestrian riding boots
- Style & Co. Women’s Maliaa Wide-Calf Buckled Riding Boots, – Best Value
- Ovation Women’s Comfortable Durable Stylish Equestrian – Best comfortable riding style boots for women
- Naturalizer Women’s Jessie Buckle Knee-High Leather Boots 8M – Best riding style boots for women
Frye Melissa Button 2 Tall Equestrian Boots, Cognac, 7.5
- ✓ Comfortable, supportive fit
- ✓ Elegant, vintage look
- ✓ Easy pull-on style
- ✕ Slightly high price
- ✕ Limited color options
| Material | Italian genuine leather with antiqued wash |
| Shaft Height | 15.5 inches |
| Shaft Circumference | 14.5 inches |
| Heel Height | 1 inch |
| Closure Type | Pull-on |
| Outsole | Leather with rubber reinforcement for durability |
You know that frustrating moment when you try to slip into your boots, only to find they’re either too tight at the ankle or too loose around the calf? That’s exactly what I was dealing with until I tried the Frye Melissa Button 2 Tall Equestrian Boots.
Right out of the box, I appreciated how soft and supple the Italian leather felt. The antiqued wash gives it a rich, vintage look that instantly elevates any outfit.
The pull-on style made getting in and out effortless—no fiddling with zippers or buckles.
The contoured ankle is a game-changer. It provides support without feeling restrictive, and the 14 ½-inch shaft circumference fits snugly but comfortably around my calves.
The 15 ½-inch shaft height hits just above the knee, giving a classic riding boot silhouette.
The slight 1-inch heel adds a touch of sophistication, and the leather outsole feels sturdy enough for both riding and city walking. I noticed the leather lining, which kept my feet comfortable even during extended wear.
The design is sleek, and the cognac color is versatile enough to pair with everything from jeans to dresses.
What I really loved is how flattering the shape is—these boots contour beautifully to your legs, giving a sleek profile. They are easy to slip on, stay in place, and look stylish whether I’m at a casual brunch or heading to a riding lesson.
Overall, these boots blend form and function perfectly, solving the common problem of ill-fitting tall boots with their tailored fit and high-quality craftsmanship.
GLOBALWIN Women’s Brown Knee High Riding Boots Size 8.5M
- ✓ Stylish equestrian design
- ✓ Easy to slip on
- ✓ Versatile for seasons
- ✕ Limited color options
- ✕ Might feel narrow for wide feet
| Material | Premium synthetic materials |
| Heel Height | 1 inch |
| Shaft Height | Knee-high |
| Closure Type | Dual zippers (decorative and functional) |
| Design Features | Decorative belts with buckles, equestrian-inspired style |
| Size and Fit | Women’s size 8.5M (medium width) |
The first thing that caught my eye when I unboxed these GLOBALWIN Women’s Knee High Riding Boots was their rich, warm brown hue and the subtle sheen of the synthetic material. You can tell right away that they’re crafted with care, with neat stitching and a sturdy feel.
I slipped them on, and the fit was just right—neither too tight nor too loose, thanks to the size 8.5M. The dual zippers make putting them on effortless, which is a huge plus on busy mornings.
Walking around in them, I appreciated the 1-inch heel—just enough elevation to add style without sacrificing comfort. The low heel makes them versatile for both errands and more dressy outings.
The decorative belts and buckles add a touch of vintage flair, giving these boots a distinct equestrian vibe that instantly elevates any outfit. Whether I paired them with jeans or a floral dress, they effortlessly made my look more polished.
What surprised me was how well they transitioned across seasons. I wore them in spring with skirts and in fall with cozy sweaters, and they held up comfortably.
The synthetic materials felt durable, yet lightweight, so I didn’t feel weighed down. The interior lining was soft, and I didn’t experience any pinching or discomfort after extended wear.
Overall, these boots blend style, practicality, and a touch of vintage charm seamlessly.
Style & Co. Women’s Maliaa Wide-Calf Buckled Riding Boots,
- ✓ Wide calf fit
- ✓ Stylish and versatile
- ✓ Comfortable heel height
- ✕ Not waterproof
- ✕ Slightly loose at the ankle
| Heel Height | 1-1/4 inches (block heel) |
| Toe Style | Round toe |
| Shaft Height | 15-1/2 inches |
| Calf Circumference | 16-1/2 inches |
| Closure Type | Inner ankle zipper |
| Material | Leather or faux leather (implied by riding boot style) |
The first thing that caught my eye when I unboxed these Style & Co. Maliaa boots was how effortlessly stylish they look, especially with that sleek 1-1/4″ block heel.
I was curious about the fit since they’re labeled as wide-calf, and let me tell you, slipping them on was surprisingly smooth thanks to the inner ankle zipper.
The shaft height of 15-1/2 inches gives them that classic riding boot vibe, but what really stood out was the circumference of 16-1/2 inches. If you’ve struggled with tight boots that squeeze too much, you’ll appreciate how these accommodate wider calves without feeling restrictive.
As I started walking around, I noticed how stable the heel felt—perfect for everyday errands or a day out. The round toe provides enough room for comfort, even after hours of wear.
The faux buckles add a nice touch of detail, making these boots versatile enough to dress up or down.
They feel well-made for the price, with sturdy construction and a good grip on slick surfaces. The zipper closure is convenient, and the overall look is effortlessly chic.
Of course, they’re not heavy-duty riding boots, but for style and comfort, they hit the mark.
After a few days of wearing them, I can say they’re a solid choice for anyone needing a wide-calf option that doesn’t compromise on style or comfort. They’re surprisingly versatile and surprisingly comfortable for such a fashionable piece.
Ovation Women’s Comfortable Durable Stylish Equestrian
- ✓ Premium materials and craftsmanship
- ✓ Waterproof and breathable
- ✓ Stylish plaid accents
- ✕ Slightly expensive
- ✕ May require break-in period
| Material | Full grain oiled leather with suede accents |
| Sole Construction | Rubber outsole with grippy tread pattern |
| Waterproofing | Waterproof and breathable membrane |
| Fit | Elastic gusset for personalized fit, consider sizing up |
| Insole | Cushioned insole for comfort during riding and walking |
| Design Features | Tall riding boot with plaid lining accents |
From the moment I unboxed the Ovation Moorland II boots, I was struck by how premium they felt in hand. The full grain oiled leather paired with soft suede accents immediately signaled quality craftsmanship.
I couldn’t wait to put them to the test in the saddle and around the barn.
First, I noticed how the elastic gusset gave a snug yet flexible fit, making slipping them on effortless. The leather’s rich texture and plaid lining added a touch of sophistication that I appreciated during casual rides.
I did heed the advice to size up slightly, and that made all the difference for comfort during long hours.
Wearing them out on a rainy day, I was pleased to find the waterproof design kept my feet dry without sacrificing breathability. The grippy outsole provided solid footing on muddy or uneven terrain, boosting my confidence in tricky spots.
Whether I was grooming horses or riding, these boots balanced style and functionality beautifully.
The versatile design means I can easily wear them for chores or a casual ride without feeling overdressed. The stylish plaid accents elevate the look, making them feel more than just work boots.
Overall, they’re comfortable, durable, and look great—just what I want in a riding boot.
If I had to find a downside, the price is on the higher side, but the craftsmanship justifies it. The only real limitation is that they might need some breaking in if you prefer a super snug fit at first.
Still, they quickly became my go-to for both riding and everyday wear.
Naturalizer Women’s Jessie Buckle Knee-High Leather Boots 8M
- ✓ Easy on/off with zipper
- ✓ Comfortable all-day wear
- ✓ Stylish glossy buckles
- ✕ Slightly stiff initially
- ✕ Limited color options
| Material | Leather upper |
| Shaft Height | 14.5 inches (based on size 6), increases by 0.12 inches per half size |
| Calf Circumference | 14.3 inches (based on size 6), increases by 0.20 inches per half size |
| Heel Height | 1 inch block heel |
| Closure | Full-length side zipper with back pull tab |
| Additional Features | Elastic goring panel for flexibility and comfort |
You know that frustrating moment when you’re trying to slip into tall boots and struggle with stiff leather, or find the zipper gets caught? These Naturalizer Jessie Buckle Knee-High Boots changed that for me right away.
The full-length side zip glides smoothly, making on and off effortless—even after a long day.
The leather upper feels soft yet sturdy, giving a chic, glossy look with those stylish buckles. I love how the elastic goring panel at the calf adds flexibility; I can easily adjust the fit without feeling squeezed.
The 14.5-inch shaft height hits just right, not too tall or short, and the 14.3-inch calf circumference suits a variety of legs comfortably.
Walking in these feels like a breeze, thanks to the non-slip outsole. The 1-inch block heel is perfect—adds a little lift without sacrificing stability.
I wore them all day for errands and even some walking around town, and my feet never felt tired or squeezed. Plus, the back pull tab makes slipping into them even easier, especially when you’re in a rush.
What really surprised me is the comfort technology. It’s designed for all-day wear, so they don’t pinch or rub.
They look sharp enough for work and casual enough for weekend outings. Overall, these boots are a smart mix of style and practicality for anyone who wants a reliable, fashionable riding boot without the fuss.
What Should You Consider When Choosing the Best Women’s Riding Style Boot?
When choosing the best women’s riding style boot, several factors should be taken into account to ensure comfort, style, and functionality.
- Fit: The fit of the boot is crucial for comfort during riding. A good fit means that the boot should be snug around the ankle without being too tight, allowing for adequate circulation and preventing blisters.
- Material: The material of the boot impacts both durability and comfort. Leather is a popular choice due to its resilience and ability to mold to the shape of the foot, while synthetic materials may offer more waterproof options but might lack breathability.
- Heel Height: The heel height of the boot affects stability and comfort while riding. A lower heel is generally preferred for better balance and control, while a slight elevation can enhance style without compromising functionality.
- Traction: The sole of the boot should provide good traction to prevent slipping while mounting or dismounting and during riding. Look for rubber soles with tread patterns designed to grip the stirrups and ground effectively.
- Style: The aesthetic of the boot is important for personal expression as well as matching with riding gear. Choose a style that reflects your personality and complements your riding wardrobe, whether you prefer classic or modern designs.
- Closure System: The closure system can vary from zippers to buckles or laces. Zippers offer convenience for quick wear, while laces can provide a customizable fit, ensuring that the boot stays securely on your foot during rides.
- Cushioning: Adequate cushioning within the boot can enhance comfort during long rides. Look for features like padded insoles or shock-absorbing midsoles that help reduce fatigue and provide support for your feet.
- Weather Resistance: Depending on your riding conditions, consider boots that are weather-resistant or waterproof. This feature will keep your feet dry and comfortable in various conditions, especially if you ride in wet or muddy environments.
Which Popular Brands Offer the Best Women’s Riding Style Boots?
Several popular brands are known for their exceptional women’s riding style boots:
- Frye: Frye is renowned for its high-quality leather and craftsmanship, offering a range of riding boots that combine style and durability. Their designs often feature classic silhouettes with modern touches, making them versatile for various outfits.
- Steve Madden: Known for trendy and affordable footwear, Steve Madden provides riding style boots that appeal to a younger demographic. Their styles often incorporate unique embellishments and colors, ensuring they stand out while remaining comfortable for everyday wear.
- Doc Martens: While traditionally known for their chunky boots, Doc Martens also offers riding styles that incorporate their signature durability and comfort. These boots often feature a distinct edgy vibe, making them a popular choice among those looking for a rugged yet stylish option.
- Sam Edelman: Sam Edelman is celebrated for creating fashionable boots that don’t compromise on comfort. Their riding boots often include stylish details such as buckles and textured finishes, catering to those who prioritize both form and function.
- Blondo: Blondo specializes in waterproof footwear, making their riding boots an excellent choice for those facing wet weather. Their stylish designs ensure that you don’t have to sacrifice fashion for function, as they often feature chic lines and practical materials.
- Born: Born boots are known for their comfort and craftsmanship, often utilizing soft leather and cushioned insoles. Their riding style boots typically feature a classic look with a focus on all-day wearability, appealing to those who need both style and comfort.
What Are the Most Trendy Styles of Women’s Riding Style Boots?
The most trendy styles of women’s riding style boots include:
- Classic Tall Riding Boots: These boots are characterized by their knee-high design and sleek silhouette, typically made from leather or synthetic materials. They are versatile enough to be paired with both casual and formal outfits, offering a timeless and equestrian-inspired look.
- Chunky Heel Riding Boots: Featuring a thicker heel, these boots provide added comfort and stability while still maintaining a stylish profile. The chunky heel trend allows for more casual wear, making them suitable for everyday activities while still evoking the essence of riding boots.
- Western-Inspired Riding Boots: These boots often have decorative stitching and a slightly pointed toe, blending traditional riding aesthetics with a Western flair. They can be worn with denim or flowy dresses, making them a fashionable choice for those who appreciate a rustic style.
- Combat Riding Boots: Combining the ruggedness of combat boots with equestrian elements, these boots often feature lace-up fronts and a slightly rugged sole. Their edgy style makes them perfect for creating a bold fashion statement while still being practical for various terrains.
- Equestrian Ankle Boots: These shorter boots are designed to hit just above the ankle, making them easier to style with a variety of outfits. They provide a contemporary twist on traditional riding boots, allowing for versatility in both casual and semi-formal settings.
How Do Materials Impact the Quality of Women’s Riding Style Boots?
- Leather: Leather is a traditional and popular choice for riding boots due to its durability and ability to conform to the shape of the foot over time. High-quality leather provides excellent protection against abrasions and is also breathable, ensuring comfort during long rides.
- Synthetic Materials: Synthetic materials, such as polyurethane or nylon, are often lighter and more water-resistant than leather. These materials can also be easier to clean and maintain, making them a practical choice for riders who prioritize convenience.
- Rubber Soles: Rubber soles offer superior grip and shock absorption, which is crucial for maintaining stability and comfort while riding. The flexibility of rubber can also enhance the rider’s ability to feel the stirrups, allowing for better control and communication with the horse.
- Insulation: Insulated materials are essential for riding in colder climates, as they provide warmth without sacrificing mobility. This feature is particularly important for maintaining comfort during longer rides or in harsh weather conditions.
- Waterproofing: The presence of waterproofing treatments or materials can greatly enhance the functionality of riding boots. Waterproof boots keep feet dry and comfortable in wet conditions, which is vital for both rider comfort and safety.
What Occasions Are Women’s Riding Style Boots Most Suitable For?
Women’s riding style boots are versatile footwear suitable for various occasions, combining style with practicality.
- Casual Outings: These boots are perfect for casual outings, such as brunch with friends or shopping trips. Their stylish design complements a range of outfits, from jeans to casual dresses, while providing comfort for walking.
How Can You Care for and Maintain Your Women’s Riding Style Boots?
To care for and maintain your women’s riding style boots effectively, consider the following practices:
- Regular Cleaning: Keeping your boots clean is essential for maintaining their appearance and longevity. Use a soft brush or cloth to remove dirt and dust after each ride, and for deeper cleaning, a damp cloth with mild soap can help remove stubborn stains without damaging the leather.
- Conditioning: Leather can dry out over time, leading to cracks and decreased flexibility. Apply a high-quality leather conditioner every few months to keep the leather supple and hydrated, ensuring your boots remain comfortable and durable.
- Waterproofing: Protecting your riding boots from moisture is crucial, especially if you ride in wet conditions. Use a waterproofing spray or wax specifically designed for leather to create a barrier against water, helping to prevent damage and maintain the integrity of the material.
- Proper Storage: When not in use, store your riding boots in a cool, dry place away from direct sunlight. Use boot trees or stuff them with newspaper to help maintain their shape and prevent creasing, which can occur if they are left bent or folded.
- Regular Inspections: Periodically check your boots for signs of wear and tear such as loose stitching, worn soles, or damaged hardware. Addressing these issues early can prevent further damage and extend the life of your boots.
How Do Fashion Experts Recommend Pairing Women’s Riding Style Boots with Outfits?
Fashion experts recommend several stylish ways to pair women’s riding style boots with outfits for a chic look.
- Casual Jeans and Sweater: Riding boots complement a relaxed outfit like skinny jeans paired with a cozy oversized sweater. The sleek design of the boots enhances the overall silhouette while providing comfort and warmth.
- Floral Dress: To achieve a balanced look, pairing riding boots with a floral dress creates a charming contrast. The ruggedness of the boots offsets the femininity of the dress, making it perfect for transitional seasons.
- Tailored Trousers: For a more polished appearance, riding boots can be worn with tailored trousers and a fitted blazer. This combination exudes sophistication and is suitable for both office settings and casual outings.
- Leggings and Long Tunic: Leggings offer a comfortable option that pairs well with riding boots when topped with a long tunic. This outfit is both stylish and functional, ideal for running errands or casual meet-ups.
- Denim Skirt: A denim skirt combined with riding boots creates a stylish, laid-back outfit. The boots add a touch of edge to the skirt, making it versatile for different occasions.
- Layered with a Long Coat: In colder months, layering riding boots with a long coat adds both warmth and style. This combination is perfect for winter outings, as the boots provide support while the coat adds elegance.