Apparel Riding

5 Comfy Tall Riding Boots That Feel as Good as They Look

comfortable tall riding boot
Written by Channing M.

The most comfortable tall riding boots can still be stylish

Developed primarily for riding, some tall english boots can be painful to wear outside of the saddle. Without proper fitting, the right materials, and an understanding of what works best for you, your first boot riding purchase can end up being an expensive mistake.

These days, you have a lot more comfortable tall boot options. In this article, we discuss boots that feel great in the stirrups, around the barn, and out on the town.

Tall Riding Boot Category Summary
Ovation Flex Sport

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Best for Calf Comfort
  • Super supple leather
  • Lots of size options
  • Versatile
Dublin Galtymore

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Best All-Around
  • Sleek fit and look
  • Steel shank protection
  • Comfortable insoles and lining
Ovation Moorland II Highrider

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Best for Active Horse People
  • Available in brown and black
  • Made for walking
  • Fabulous for all-day wear
Ariat Heritage Contour II

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Best Classic Boot
  • Wide range of sizing options
  • Traditional styling
  • Flexibility is built-in
TuffRider Ladies SureGrip

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Best Security in the Saddle
  • Secret grippy superpowers
  • Look long and sleek
  • Need a little more break-in time

Ovation Flex Sport Field Boot

This field boot is a favorite of riders who enjoy straight-from-the-box boot suppleness. Ovation’s Flex System utilizes a design that provides not only maximum ankle movement, but also correct stirrup position. The flexibility and soft leather provide a pleasant experience on the ground, as well.

ovation flex sport boot

Click to see details at State Line Tack

The Flex Sport’s field boot styling is good for nearly all English riding disciplines. These boots hold up well, especially against mud, sweat, and other dirt with a quick wipe down. (Shouldn’t everything be that easy?)

The Ovation size range is quite generous, covering calf sizes from slim to XX-wide.


  • Soft supple cowhide with pigskin cuff lining
  • Stretch panels on inside of zipper allow more give easier fit for calves
  • Widths from Slim to XX-Wide accommodate all body types
  • Flex System allows for full movement of your ankles right out of the box


  • Can run a little wide for those with narrow feet/skinny calves
  • Ripple sole lacks extra cushioning

Click to see this boot at State Line Tack

Dublin Galtymore Dress Boot

Always on top of the boot game, Dublin has created a standout option with this versatile Galtymore Dress style. Made of full-grain leather with a Spanish top (Hello, leg-lengthening magic!), these sleek beauties are super flattering.

dublin galtymore boot

Click to see details at State Line Tack

On the inside, the Galtymore is all about comfort. They have an RCS Ultra footbed that’s both shock-absorbing and moisture-wicking. A zipper gets you into the contoured fit without an embarrassing struggle, and there’s also an elastic panel to permit just enough give.

Plus, next time your beloved steed forgets your foot is there, you’ll love the built-in steel shanks.


  • Sleek and svelte
  • Steel shank protection for those barn mishaps that always happen
  • Regular and Tall heights available


  • The close-fitting ankle may feel confining to some riders
  • More pointed toe than some other dressage boots, which may be an issue if you want more toe wiggle room

Click to see this boot at State Line Tack

Ovation Moorland II Highrider Boot

Some horse people have days with as much time on the ground as in the saddle. For these hard-working souls, we present the Moorland II. The thick, shock-absorbing rubber sole is designed for good grip and easy stirrup entry.

Look closely, and you’ll see that the suede upper is perfectly matched with the oiled leather foot. The overall effect is that of a traditional tall english riding boot.

ovation moreland ii highland boot

Click to see details at State Line Tack

These are perfect for barn owners, riding instructors, and other busy equestrians. They’re easy to get on and off with a zipper. They’re easy to clean with minimal fuss. They’re even waterproof in the foot, thanks to the breathable membrane liner.

They’re also cute with jeans – just saying!


  • Come in black or brown
  • Practical, bouncy rubber outsoles
  • Roomy toe box


  • Not for showing
  • A more relaxed calf fit could feel sloppy

Click to see this boot at State Line Tack

See why the Highrider also made our list of the 5 Best Boots for Long, Hard Days at the Horse Barn.

Ariat Heritage Contour II Field Zip

The Heritage, as you might guess from the name, is a traditionally-styled field boot with great modern updates. Ariat has always focused on foot comfort, and this boot proves it.

It features Ariat‘s 4LR footbed system for support and cushioning. On the ground, the Duratread outsole is shock-absorbing. In the saddle, it’s configured to provide the right amount of stirrup traction.

Note: Ariat also makes a short riding boot that we love! Check out the Heritage paddock boot 

ariat heritage contour

Click to see details at State Line Tack

The leathers used in the Heritage are supple, and break-in time is minimal. There’s lots of “give” in the design, which results in a snug but elastic feel to the boot, down to the laces. The inner calf is also gusseted and elasticated, allowing the boot to move with you.


  • Classic field boot
  • Specialized outsole design
  • Wide range of size options, including Short and XX-Slim


  • Extensive sizing chart might be hard to navigate
  • Might feel snug at ankle, due to a more contoured fit

Click to see this boot at State Line Tack

TuffRider Ladies SureGrip Tall Boots

Just a little bit of extra grip on a field boot? You got it! TuffRider has thoughtfully added a sneaky helper to this boot style: a natural rubber inset on the inner upper shaft. That certainly provides mental comfort, but there’s more to love.

tuffrider ladies suregrip boot

Click to see details at State Line Tack

The Spanish Style uppers give you that long-legged look in the saddle, while the elastic gussets in these boots keep them from feeling too tight. Well-designed flex construction lets ankles have a full range of motion in the saddle and on the ground. Back zippers keep you pulled together and snug, from the stall to the arena.

You might even find yourself feeling a bit more confident as you walk around the barn!


  • Subtle extra grip
  • Sleek design
  • Attractive matte black finish


  • May take a little time to fully break in
  • Fewer size options and only one height available

Click to see this boot at State Line Tack

Frequently Asked Questions

What are the most comfortable riding boots?

Look for a middle ground between walking and riding features, and for supple full grain leather. The most comfortable tall leather boots will provide a snug fit without feeling like your circulation is impaired. Gussets and elastic can make or break the fit of your boots and how much you’ll wear them.

comfortable tall riding boots

Source: Emily Harris

Features like comfort insoles and rubber soles can be more important if you’re doing a lot of work on the ground. In the calves, the right size is vital – be sure to follow size charts and measure correctly.

If you’re just starting your search, we suggest beginning with the Ovation Moorland Highrider leather boots.

What riding boots are best overall?

Field boots will get you through most English classes – but the best overall boots are the ones you actually enjoy wearing. Once they’re broken in, you should feel perfectly comfortable walking around, as well as when you’re riding.

Key features like a snug fit, supportive insoles, and flexibility where you need it (e.g. ankle) should be on your checklist.

The Ovation Flex Sport Field Boot is a perfect overall option!

How should tall riding boots fit?

First of all, try them on with the breeches and socks you’ll usually be wearing. The boots should be snuggly, in a good way. They shouldn’t be too loose or have big gaps. When new boots settle in and begin to “drop,” overly loose uppers can create wrinkles around your ankles that are uncomfortable.

For field boots and dressage boots, new pairs will hit high on your leg, with the top in the middle of your kneecap. (Remember, it’s going to drop a little as it breaks in.) Boots used for dressage will be a little lower – just under your kneecap.

Are tall boots supposed to be tight?

They should be snug, but not uncomfortably so. It’s a good sign if they’re a little bit difficult to pull on and off, but not so tight around your calves that they cut off circulation.

How do you shrink tall riding boots?

It’s much easier to stretch riding boots. If your boots are too big, it’s best to consult a local shoe and boot repair shop for guidance.

Walk Tall (And Comfortably)

A good tall boot is similar to a good relationship: supportive, close, but not suffocating, and super comfortable. Also, as with dating, don’t fall for the first one you see. Take the time to take accurate measurements, make sure they feel good on your foot, and allow for break-in time.

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About the author


Channing M.

When I'm not using my equine anatomy, physiology, veterinary care background to educate other equestrians, you'll find me volunteering with retired racehorses or vacationing in the Gulf of Mexico with my hubby and beach-loving lab.