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8 Most Comfortable Tall Horse Riding Boots for Equestrians

Tall boots can be great for riding, but sometimes it can be hard to find a pair that fits well. We are sharing the eight most comfortable tall riding boots for equestrians that will keep your feet happy as you ride.

When it comes to tall boots, you want a pair that is practical and chic. Good riding boots are an investment, but it is important to have quality equipment when riding. You don’t want to buy a pair of boots just because they are cheap, only to have them break within a couple of months.

How to Choose the Right Pair of Tall Riding Boots

Before you go shopping, there are some factors you need to take into consideration when buying your boots. When choosing tall boots, you need to consider comfort, durability, discipline, safety and material.

Comfort: A good pair of tall boots will be designed to comfortably fit your foot and calf. In addition, you want to look for features like a cushioned insole and breathable mesh lining.

Durability and Safety: Tall boots should be both durable and flexible. They should be able to hold up for several years without ripping.

Discipline: There are different styles of tall boots depending on the discipline. The three main kinds are field, dress and dressage. There are also work and schooling boots that are practical for training.

Field boots are worn in hunter/jumper disciplines, lower level dressage and eventing. They are made from soft, supple leather and have signature laces on the insteps.

Dress boots are worn in formal hunter classes and jumpers, as well as lower levels of dressage. They are soft and supple but do not have laces. Dressage boots are worn in all levels of dressage. They are stiffer, have no laces, and have a straighter, stovepipe fit.

Material: Tall boots should be made from leather or high-quality synthetic material. They should be easy to break into, so you don’t have to deal with blisters or rubs.

Most Comfortable Tall Horse Riding Boots

1. TuffRider Starter Field Boots (Womens)

TuffRider Ladies Starter Field Boots

Made from synthetic leather, these vegan tall riding boots are extremely flexible and will keep you comfortable all day long. Designed with an immediate break-in, you can concentrate only on your riding without worrying about getting rubs or blisters.

The water-resistant design is great for all seasons and weather conditions. Thanks to the elastic gusset and full zipper back, they contour nicely to your calves. The flex construction performance footbed gives you the support you need, while the Spanish-style top provides a traditional, elegant look.

Why We Like Them:

  • Immediate break-in for ideal comfort.
  • Extremely flexible with a weather-resistant design.
  • Elastic gusset and flex construction performance footbed for support.

2. Ariat Coniston Pro GTX Insulated Country Boot (Womens)

Ariat Coniston Pro GORE-TEX Insulated Boots

If you are looking for a pair of tall schooling boots, look no further than these Ariats. Right of the box they are comfortable and will keep your feet protected no matter if you are riding or walking.

With a zipper in the back along with a full-length lace-up in the front, you can adjust them just right to get a secure fit. The premium full-grain leather is durable and waterproof, which is wonderful for any weather. They have a breathable GORE-TEX membrane construction, ATS Pro technology footbed with composite forked shank, and Duratread rubber sole to give you support and traction. The unique Thinsulate Insulation provides warmth in winter with less bulk.

Why We Like Them:

  • The back zipper and front laces allow for a secure fit, which is great for riding and walking.
  • Premium leather is waterproof.
  • The breathable mesh lining, ATS foot and rubber outsole provide support and comfort.

3. Dublin River Boots III (Womens)

Dublin Women's River Boots

For a stylish, yet practical tall schooling boot, Dublin comes through with quality and support. The genuine leather grain on the outside and nylon lining on the inside create optimal comfort and durability.

For premium arch support, there are double layers of cushioning that help relieve pressure and long-term pain on your heels. The waterproof design keeps your feet dry all year long, whether you are riding, doing barn chores or walking. With the Tough Tec outer rubber outsoles, you eliminate the risk of slipping or sliding while allowing for flexible movement.

Why We Like Them:

  • Practical for riding, walking, and barn chores.
  • Waterproof leather exterior and breathable nylon are durable and supportive.
  • Double layer cushioned footbed and rubber outsoles for comfort and flexibility.

4. Ovation Moorland II Highrider Boot (Mens)

Ovation Mens Moorland II Highrider horse riding Boot

These versatile tall boots are great for riding, barn work, and even hiking. A full-grain oiled leather foot is paired with a grippy suede upper to create a durable boot capable of withstanding all seasons.

A full-length zipper and an upper elastic gusset create a superb fit. With a breathable waterproof membrane and a moisture-wicking Dry-Tex lining, your feet will be cool and dry. The sturdy grippy outsole provides exceptional support and traction in all conditions.

Why We Like Them:

  • Great for riding, barn chores, and everyday wear.
  • Made from durable leather and a grippy suede upper, with an elastic gusset for superior fit.
  • Waterproof and breathable, with a grippy outsole for traction.

5. TuffRider Baroque Dress Boots (Mens)

TuffRider Men's Baroque Dress Boots

With a traditional style, these boots are well-made and come in at an affordable price. They feature a Spanish toe and top for a classic look.

With a full-length back zipper and elastic gusset, they have freedom of movement and a secure fit. The soft, supple leather is comfortable and practical for riding. A memory foam footbed provides premium comfort to keep your feet happy at the barn.

Why We Like Them:

  • Traditional style at an affordable price.
  • Full-length back zipper and elastic gusset provide freedom of movement.
  • Quality leather exterior and a comfy memory foam footbed.

6. EQUISTAR All-Weather Synthetic Field Equestrian Boot (Womens)

EQUISTAR Women's All-Weather Synthetic Field Equastrian Riding Boot

These synthetic field boots are a lovely affordable option compared to classic leather boots that can cost hundreds of dollars. Their all-weather design makes them ideal for wearing no matter if it is snowing or raining out.

For superior moisture management, the shaft of the boot is cushion-lined with the signature Dry-Tex technology. The EquiStar Sole System is designed to provide additional comfort with its reduced weight and improved flexibility. Built with a very narrow profile and V-style gussets at the top, they are made to contour to your leg for a superior fit.

Why We Like Them:

  • Affordable and made from soft, synthetic leather.
  • All-weather design is great for wearing all-year-round.
  • Moisture management Dry-Tex and Equistar Sole System make for a comfy fit.

7. Ariat Heritage Contour II Field Zip Tall Riding Boot (Womens)

Ariat Women's Heritage Contour II Field Zip Tall Riding Boot

With a classic field style combined with Ariat’s innovative design, these boots are sleek and supportive. The elegant leather build is both durable and stylish looking, which is great for everyday riding and the show ring.

The 4LR footbed system and ultra-contoured fit through the ankle make for superior comfort while horseback riding. With a moisture-wicking sock liner, your feet will stay cool even on the hottest summer days. The full-length elasticized panel on the lateral side, elastic gusset on the inside knee and elasticized laces create a secure and custom fit. Thanks to the Duratread outsole you will have traction and flexibility both in and out of the saddle.

Why We Like Them:

  • High-quality leather makes them durable and elegant.
  • 4LR footbed, contoured fit, elastic gusset, and moisture-wicking liner make for a comfortable fit.
  • Duratread outsole provides traction and flexibility.

8. TuffRider Lexington Waterproof Tall Country Boots (Mens)

TuffRider Men's Lexington Waterproof Tall Country Boots

From riding to mucking stalls, these tall riding boots are great for beginners. No matter the weather, the weatherproof design keeps your feet dry while the rubber soles ensure you have safe footing even in wet conditions.

With a sturdy leather build, they are durable and supple, which is ideal for wearing to the barn. The elastic gussets and drawstring closure allow for a secure fit. The padded memory foam insoles provide the support your feet need to keep them comfortable for hours on end.

Why We Like Them:

  • The leather exterior and lining are waterproof.
  • Durable and versatile, with elastic gussets and drawstring closure for an ideal fit.
  • Padded memory foam insoles provide top-notch comfort.

Frequently Asked Questions

How Are Tall Riding Boots Supposed to Fit?

When worn with socks and breeches, tall boots should fit snugly. There shouldn’t be any big gaps, as that would create an awkward fit. Field and dress boots will hit high on your leg when you first get them, with the top curve hitting at the middle of your kneecap. Dressage boots will fit a bit lower and have a slightly stiffer construction. Over time, they will drop a small amount as you break them in.

Are Tall Riding Boots Supposed to Be Tight?

Tall boots should fit snugly, but not be tight in the calf. If they are too tight in the calf, they can cause discomfort while riding. If you have a hard time zipping up your boots, you may want to opt for a pair with a wider fit. Having a properly fitting boot is important when riding, as it will be more comfortable and give you more flexibility.

Are Short or Long Riding Boots Better?

Short and long riding boots are both great for riding. Many people decide between the two by personal preference. Short boots, aka paddock or jodphur boots, are often more affordable and can be worn with half chaps if desired. However, some people prefer the fit and extra protection tall boots provide from chafing when riding hunter/jumper, eventing or dressage.

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