Apparel Gear

7 Comfiest Cowboy Boots That Won’t Leave You Flat Footed

Cowboy boots
Written by Natalie Gasper

Don’t Let Flat Feet Frustration Spoil Your Fun

Western boots and flat feet don’t mix… or do they? Check out these options for flat-footed cowboys and cowgirls everywhere.

Focus on brands that provide comfortable insoles and arch support. Ariat is a solid brand thanks to their ATS technology. Any boot with a square toe is a good choice because it gives your feet plenty of room. Look for boots with a shock-absorbing insole. When in doubt, you can also replace the factory insole with a more supportive one designed for flat feet.

Boot Basics: What to Look for in a Riding Boot

One of the most important things to look for is comfort. If the flashy boot makes your feet ache or your heels bleed, you won’t be wearing them for long!

You also want a one-inch heel to prevent your foot from slipping through the stirrup.

Additional Considerations for Flat Feet:

  • Shock-absorbing capabilities
  • A thick sole that is firm yet flexible
  • Consider replacing the factory insole with something more supportive

Our Picks for Flat Feet

Category Option Price Point Key Features
Best Overall Boot Ariat Women’s Remuda $$$$ Full-grain leather, very stylish
Best Men’s Boot Ariat Men’s Hybrid Street Side $$$ Non-slip sole, classic design
Best Women’s Boot Ariat Women’s Heritage Fatbaby $$ Pure leather, great for riding
Best for Summer Laredo Women’s Keyes Patriotic Snip Toe $$$ Stars and stripes design, quality leather
Best for Winter Ariat Terrain Pull-On Waterproof Boots $$$ Multipurpose, lightweight yet durable
Best on a Budget Justin Original Men’s Stampede Work Boots $$ Great for riding and working, high-quality materials
Best for a Splurge Tin Haul Ladies South by SW Square Toe Boots $$$$ Hand-painted, premium cow leather lining

Ariat Women’s Remuda

Ariat is the queen of comfort when it comes to riders with flat feet, thanks to their innovative ATS technology.

This boot combines arch support with a fashionable design.

ariat remuda boot

Click to see them at Amazon


  • Leather boot paired with a non-slip rubber sole
  • Great for work and fashion (looks good with dresses, skirts, jeans, etc.)
  • No break-in necessary


  • The inside of the boot is pink

See them at Amazon

Ariat Men’s Hybrid Street Side

Ariat created the best of both worlds thanks to the four-layer footbed designed for maximum comfort.

These boots are exceptionally tough yet provide airflow for ventilation.

ariat hybrid boot

Click to see them at Amazon


  • Hybrid style design works great for the barn and going out
  • Square toe (perfect for flat feet)


  • May require a LONG break-in period

See them at Amazon

Ariat Women’s Heritage Fatbaby

Ariat is a go-to brand for those with flat feet thanks to their ATS arch support technology. These boots will cradle your feet and are comfortable to wear all day long.

They can also be a little bit cooler to wear in the summer, as they have a shorter design.

ariat fatbaby

Click to see them at Amazon


  • Beautiful combo of leather and suede
  • Wide, square(ish) toe box
  • Suitable for wide and flat feet


  • Needs a break-in period

See them at Amazon

Laredo Women’s Keyes Patriotic Snip Toe

Nothing says summer like this red, white, blue, and tan boot, perfect for a night on the town.

The cushioned insoles provide arch support while keeping you happy on your feet.

laredo keyes boot

Click to see them at Amazon


  • Distressed leather look
  • Soft and supple
  • Looks great with jeans, skirts, or shorts


  • Not the best fit if you have large calves

See them at Amazon

Ariat Terrain Pull-On Waterproof Boots

These waterproof boots are perfect for keeping your feet warm and dry in winter. Built for snow, muck, and rain, they’ll keep up in any work environment.

An added bonus? They’re great for both chores and riding.

ariat terrain boot

Click to see them at Amazon


  • EVA midsole is shock-absorbing
  • ATS arch support technology
  • High-traction sole


  • The sole lacks the traditional Western look

See them at Amazon

Justin Original Men’s Stampede Work Boots

While this boot is designed for men, it can also work quite well for women.

The J-flex system is perfect for riders who are on their feet all day.

justin stampede boot

Click to see them at Amazon


  • Sturdy, non-slip sole
  • Removable insole (perfect if you need more or less support)
  • Wide, square toe


  • Some users report the leather irritated their skin. Thick socks are a good workaround.

See them at Amazon

Tin Haul Ladies South by SW Square Toe Boots

While you could wear these shoes for barn work, you won’t want to. These fashionable boots are perfect for a night out! The multi-colored design is stunning, and the square toe provides plenty of room for those with flat feet.

Tin Haul puts fun designs on their boot’s soles as well as the more visible parts—be sure to check out the added touch on this pair!

tin haul boots

Click to see them at State Line Tack


  • Low heel (suitable for riding)
  • Easy pull-on straps
  • Stunning design


  • You’ll need some time to properly break them in

See them at State Line Tack

Spotlight: Blackrock Leather ‘N’ Rich

Looking for a leather cleaning alternative to saddle soap, mink oil, conditioners, and preservers? Blackrock was founded in 1976 and quickly become a household name—for good reason.

Not only does it breath new life into any finished leather product, Blackrock products are made in the USA. Blackrock is safe to use on boots, shoes, saddles, tack, furniture, car interiors, and everything in between. (Note: Don’t use it on suede or nubuck.)

Plus, the company pledges 1% of sales to the preservation and restoration of the natural environment.

“If it’s leather… use Blackrock!”

Click to see Blackrock Leather Care Products

blackrock leather cleaner

Blackrock Complete Leather Care Kit

blackrock leather cleaner review

Here’s a leather jacket that hadn’t been cleaned in 20 years after a single Blackrock application!

Frequently Asked Questions

Q: Which style of cowboy boots are most comfortable?

For everyday use, roper-style cowboy boots are the most comfortable, thanks to their low heel and short shafts.

Q: Are cowboy boots good for arches?

Technically, no. Cowboy boots lack a midsole, which is what provides arch support. Most people have no problem with this unless they have flat feet or plantar fasciitis.

Q: Can you wear cowboy boots with flat feet?

This depends on your foot and the boot you choose. People with flat feet will benefit from an arch-support insole.

Q: What cowboy boots are good for flat feet?

If you have cowboy boots, stick with brands like Chisos, Ariat, and Tecovas. All three make cowboy boots with the flat-footed in mind.

Parting Thoughts

Don’t let flat feet stop you from enjoying a well-crafted pair of cowboy boots. Whether you choose a brand that’s designed for flat feet or opt to use an insole in a different brand, there’s an option out there for everyone.

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About the author


With a bachelor's degree in creative writing from the University of Central Florida and an editing certificate from the University of Washington, my decade-long writing journey has been a kaleidoscope of diverse experiences. I've had the privilege of contributing to a spectrum of platforms, including newspapers, print and online magazines, literary journals, and individual clients on subjects spanning from horse care, gardening, motorcycles, to exploring East Asia.