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The 3 Best Cowboy Boots for Horseback Riding

Last updated: November 21, 2023

By: Miles HenryFact Checked

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Owning the best cowboy boots for horseback riding is essential for any Western riding enthusiast. This article explores the top three choices: Justin Men’s Ropers, ARIAT Men’s Heritage Roper Cowboy Boots, and Dan Post Boots Milwaukee Round Toe.

Each of these boots is renowned for its quality, comfort, and durability, making them ideal for riders seeking the best in performance and style. Whether you are a seasoned rider or just starting out, this guide will help you understand what makes these boots stand out and how to choose the right pair for your horseback riding adventures.

Picture of my Tecovas cowboy boots
Tecovas “The Doc”

Quick Update: Just started riding in these Tecovas “The Doc” boots – you can see them above. They are comfortable and really well-made. They’re ticking all the right boxes for what I need in riding boots. I’ll give you a full review on them after riding around in them for about six months, so stay tuned!

Update: I recently started riding in Tecovas “The Doc” boots, pictured above. They are exceptionally comfortable and well-made. So far, they are impressive cowboy boots; check all the boxes you need in a good pair of riding boots. I’ll write more about them after I’ve ridden in them for six months.

Justin Men’s Ropers

Justin Men’s Ropers are popular among horseback riding enthusiasts known for their exceptional quality and classic design. Crafted with premium leather, these boots offer durability and comfort, essential for long rides. The boots feature a low, walking-style heel and a rounded toe, which provide stability and ease of movement in the stirrup.

Additionally, they are equipped with a cushioned insole and a flexible midsole, enhancing comfort during extended wear. The outsole is designed for grip and balance, which is crucial for maintaining control while riding. Their simple yet elegant style makes them versatile and suitable for riding and casual wear.

Pros:

  • Durability: Made with high-quality leather, these boots are built to last, resisting wear and tear from regular riding.
  • Comfort: The cushioned insole and flexible midsole offer superior comfort, ideal for long days on horseback or the ground.
  • Stability: The rounded toe and low heel provide stability in the stirrup, making them safe and reliable for riding.
  • Versatility: Their classic design allows them to be worn in various settings, from the ranch to casual outings.

Cons:

  • Break-In Period: Some users report a break-in period before the boots reach optimal comfort.
  • Limited Style Variations: While classic, the style options are somewhat limited, which may not appeal to those seeking more modern or flashy designs.
Picture of Justin roper deerskin boots, which I really like for horseback riding.
Justin Ropers

Customers praise Justin Men’s Ropers for their exceptional comfort and durability. One rider mentioned, “After a month of daily use, they molded perfectly to my feet, offering unparalleled comfort.” Another user highlighted their practicality: “They’re not just great for riding but also everyday chores around the farm.” However, a few noted the initial stiffness, with one customer advising, “Give them some time to break in. Once they do, you won’t want to take them off.”

Here are links to my three favorite Justin Boots for sale on Amazon’s site so you can check their prices and also read their customer reviews:

ARIAT Heritage Roper Cowboy Boots

The ARIAT Heritage Roper Cowboy Boots are renowned in the Western riding community for their exceptional blend of traditional style and modern technology. These boots are designed with a full-grain leather upper, providing elegance and durability.

A key feature is ARIAT’s Advanced Torque Stability (ATS) technology, which supports and cushions the foot as you move, promoting good posture and reducing fatigue. The boots also feature a Duratread™ outsole that offers lasting performance, excellent traction, and flexibility.

The toe design adds to the modern cowboy look and offers additional room and comfort for the toes. These boots are not just functional; their polished look suits them for riding and social occasions.

Pros:

  • Advanced Comfort: ATS technology provides superior comfort and stability, making them ideal for long rides or days on your feet.
  • Durability: Crafted with high-quality materials, these boots are designed to withstand the rigors of frequent use.
  • Versatility: Elegant enough for social events yet rugged enough for riding, these boots cater to various needs.
  • Traction: The Duratread™ outsole ensures excellent grip, which is essential for safety while riding.

Cons:

  • Price: They are a bit pricier, which might be a consideration for budget-conscious buyers.
  • Weight: Some users find them slightly heavier than other cowboy boots, which could be a factor during prolonged wear.
These Ariats are often considered the best cowboy boots for horseback riding.
My Ariat Ropers

User Feedback

Users frequently praise the ARIAT Men’s Heritage Roper Cowboy Boots for their comfort and durability. One reviewer noted, “They’re worth every penny. Comfortable right out of the box and they hold up well over time.”

Another user commented on their versatility, stating, “These boots are as good on the ranch as they are in a restaurant.” However, a few reviews mentioned the weight, with one customer saying, “They’re a bit heavy, but you get used to it, and the quality is unbeatable.”

Dan Post Boots Milwaukee Round Toe

Dan Post Boots Milwaukee Round Toe are a standout choice for horseback riders who value style and functionality. These boots are crafted with intricate stitching and high-grade leather, showcasing a blend of traditional craftsmanship and contemporary aesthetics.

The round-toe design contributes to a sleek and timeless look and offers ample room for comfort. One of the distinctive features of these boots is their Comfort Cushion insole, designed to provide superior comfort and support, particularly beneficial during long rides.

Additionally, the boots are equipped with a durable outsole that offers good traction and stability, essential for safe and effective riding. The Milwaukee boots are not just practical for riding; their stylish design makes them suitable for various occasions, from casual outings to more formal events.

Advantages:

  • Supreme Comfort: The Comfort Cushion insole ensures long-lasting comfort, reducing foot fatigue.
  • Durable Construction: Made with premium materials, these boots are built to last and withstand regular use.
  • Versatile Style: Their elegant design makes them suitable for various settings, from the barn to social gatherings.
  • Good Traction: The outsole provides a reliable grip, which is essential for riding safety.

Limitations:

  • Fit Issues: Some users have noted that sizing can be tricky, advising them to try them on before purchasing or to consult size charts carefully.
  • Maintenance: The high-grade leather requires regular care to maintain its appearance and longevity.

Customer Reviews

Customers often rave about the comfort and style of Dan Post Boots Milwaukee Round Toe. “These are the most comfortable boots I’ve owned,” one reviewer stated, highlighting their suitability for all-day wear.

Another mentioned, “They look great for any occasion and have held up really well.” However, a few customers have mentioned the importance of getting the right size, with one saying, “Make sure to check the sizing; they run a bit large, but once you get the right fit, they’re perfect.”

Comparison Section: Justin Men’s Ropers vs. ARIAT Men’s Heritage Roper Cowboy Boots vs. Dan Post Boots Milwaukee Round Toe

In this section, I compare the Justin Men’s Ropers, ARIAT Men’s Heritage Roper Cowboy Boots, and Dan Post Boots Milwaukee Round Toe in terms of comfort, durability, style, and price. This comparison will help determine which boot might be best for different types of riders.

Feature/BootJustin Men’s RopersARIAT Men’s Heritage RoperDan Post Boots Milwaukee Round Toe
ComfortGood (improves with break-in period)Excellent (ATS technology for support and reduced fatigue)Superior (Comfort Cushion insole for immediate comfort)
DurabilityHigh (quality leather, resists wear)Very High (Duratread™ outsole, robust construction)High (premium materials, requires maintenance)
StyleClassic, understated cowboy look; limited style variationsTraditional with a modern touch; versatile for various eventsSleek, intricate stitching; suitable for casual to formal
Price RangeMid-rangeHigher-end (reflects technology and durability)Mid to high (varies by style and design)
Best ForRiders seeking a durable, classic bootRiders needing foot support, versatile useRiders prioritizing immediate comfort and style

Comfort

  • Justin Men’s Ropers: Known for their cushioned insole and flexible midsole, these boots offer significant comfort once broken in, ideal for long rides and everyday wear.
  • ARIAT Men’s Heritage Roper: These boots stand out with their Advanced Torque Stability technology, providing excellent foot support and reducing fatigue, making them suitable for riders who spend a lot of time on their feet.
  • Dan Post Boots Milwaukee Round Toe: Highlighted for their Comfort Cushion insole, they are praised for immediate comfort, suitable for riders who prioritize comfort from the first wear.

Durability

  • Justin Men’s Ropers: Made with high-quality leather, these boots are durable and resist wear and tear, suitable for frequent riders.
  • ARIAT Men’s Heritage Roper: The Duratread™ outsole and robust construction make these boots highly durable and ideal for rugged use.
  • Dan Post Boots Milwaukee Round Toe: Crafted with premium materials, these boots are also durable but require regular maintenance to keep their appearance.

Style

  • Justin Men’s Ropers: Offer a classic, understated cowboy look, versatile for various occasions but with limited style variations.
  • ARIAT Men’s Heritage Roper: Combine traditional design with a modern touch, making them adaptable for riding and social events.
  • Dan Post Boots Milwaukee Round Toe: Known for their intricate stitching and sleek design, these boots are stylish and suitable for various settings, from casual to formal.

Price

  • Justin Men’s Ropers: Generally priced mid-range, offering good value for their quality.
  • ARIAT Men’s Heritage Roper: Tend to be pricier, reflecting their advanced technology and durability.
  • Dan Post Boots Milwaukee Round Toe: Price varies depending on style and design, usually ranging from mid to high cost.

Best Fit for Different Types of Riders

  • Justin Men’s Ropers: Ideal for riders looking for a durable, classic boot that becomes more comfortable over time.
  • ARIAT Men’s Heritage Roper: Best for riders who need extra foot support and are willing to invest in high-quality, versatile boots for riding and everyday use.
  • Dan Post Boots Milwaukee Round Toe: Perfect for riders who prioritize immediate comfort and style and are prepared to maintain the boots’ appearance.

Buying Guide: Selecting the Best Cowboy Boots for Horseback Riding

Choosing the proper cowboy boots for horseback riding is crucial for comfort and safety. Here are key factors to consider when making your selection:

1. Fit

  • Proper Sizing: Ensure the boots fit snugly around your foot, with space in the toe area. They shouldn’t be too tight or too loose.
  • Heel Slippage: Expect some heel slippage initially; this is normal until the boots are fully broken in.
  • Width and Arch Support: Consider the width of the boot and the arch support it offers, especially if you have specific foot needs.

2. Material

  • Leather Quality: High-quality leather lasts longer and molds to your feet over time, offering a custom fit.
  • Breathability: Choose materials for good air circulation to keep your feet comfortable during long rides.

3. Sole Type

  • Leather Soles: Traditional and slick, they are great for riding but offer less grip when walking.
  • Rubber Soles: Provide more traction and are generally more durable and comfortable for extended wear. However, soles that are too thick will get caught in stirrups.
  • Traction and Stability: If riding is your primary purpose, choose soles that are easy to get in and out of stirrups.

4. Personal Style Preferences

  • Design and Color: Cowboy boots come in various designs and colors. Select a style that reflects your taste and complements your riding attire.
  • Functionality vs. Fashion: Determine whether you prioritize boots for their functional aspects (riding, farm work) or as a fashion statement.

5. Boot Height and Toe Shape

  • Shaft Height: The shaft should be high enough to protect your legs from chafing against the saddle.
  • Toe Shape: Round toes are generally more comfortable for riding, while pointed toes are more traditional and fashionable.

6. Price and Quality

  • Investment in Quality: Higher-priced boots often offer better quality and durability, but there are also good options at mid-range prices.
  • Long-Term Value: Consider your boots as an investment. Quality boots can last for years, making them worth the upfront cost.

7. Break-In Period

8. Reviews and Recommendations

  • User Experiences: Read reviews and ask for recommendations from experienced riders to get insights into the longevity and performance of the boots.

Remember, the right cowboy boots are not just about style – they’re an essential part of your riding gear, contributing to your comfort, safety, and riding experience. Take the time to choose boots that meet your needs and preferences.

Why “Ropers” For Horseback Riding

My favorite style of Western boots for horseback riding is “ropers.” There are a couple of reasons I prefer them; first, ropers have a shorter shaft than traditional cowboy boots. The shaft typically rises two to three inches above your ankles, as opposed to mid-calf in traditional boots. Boots with short shafts are cooler, easier to slide your foot into, and less cumbersome when walking.

The downside is you have a smaller portion of your lower leg protected when riding. But since we live in such a hot climate, I favor the short shaft over the traditional shaft length. “Ropers” typically have a one-inch heel which is closer to standard shoe heels. Because of the similarity in height to a regular shoe heel, the “roper” heel is more comfortable for walking than regular cowboy boots.

However, the heel is not so short that it fails to fit the stirrup of the saddle safely. Ropers come in a variety of soles, depending on your preference. You can purchase ropers with rubber, composite, or leather soles. For riding, I prefer leather soles because they don’t grip the stirrup.

Traditional “ropers” have a round toe, but they can also be purchased in square-toe designs. I like round-toed boots, but for practical purposes, there is no difference.

Picture of me wearing Ariat Amos square toe cowboy boots.
Ariat Amos Cowboy Boots

Honorable Mention: Ariat Amos Cowboy Boots

I just bought a pair of Ariat Amos cowboy boots, and I have to say I’ve been impressed. I’ve always liked Ariat boots, and I own a few pairs, including ropers and work boots. But overall, these may be my new favorite riding boots. They have a sole with decent traction, so when you’re not riding, you’re not slipping. But the sole isn’t so thick that getting in and out of a stirrup is difficult.

The shank is higher than a traditional roper but not by much, and it’s made with the new shock shield technology for added heel comfort. I definitely recommend these boots for riding and general use.

Below is a YouTube video that discusses horse-riding boots.

YouTube video

Conclusion

Selecting the best cowboy boots for horseback riding requires careful consideration of fit, material, sole type, and personal style. Whether you choose Justin Men’s Ropers for their classic design, ARIAT Men’s Heritage Roper for advanced comfort, or Dan Post Boots Milwaukee Round Toe for immediate wearability and style, it’s essential to invest in boots that meet your specific riding needs.

By focusing on quality, comfort, and functionality, you’ll ensure a safe, comfortable, and enjoyable riding experience. Remember, the right pair of boots can significantly enhance your horseback riding adventures.

FAQ

Will my cowboy boots stretch?

Yes, cowboy boots are made to stretch and form to the shape of your feet. I wrote an article on this topic you may find helpful to read before buying a pair of cowboy boots: Do Cowboy Boots Stretch and Mold to Your Feet?

Will cowboy boots get ruined in the rain?

Cowboy boots, especially those made of leather, can be damaged by rain if not properly cared for. Water can cause the leather to dry out and crack over time. However, immediate damage isn’t likely. After wearing them in the rain, clean and dry them thoroughly. Use a conditioner or waterproofing treatment to extend their lifespan.