Apparel Tips

Hobbling is for Horses: 7 Most Comfortable Cowgirl Boots

cowgirl boot gal riding horse
Written by Horse Rookie

You don’t have to sacrifice cuteness for comfort.

Looking good and feeling good — shouldn’t you be able to do both? We think so, which is why we put together a list of comfiest cowgirl boots.

Whether you’re dressing up for a western-style wedding, heading to the office, grabbing drinks downtown, or working the ranch, your feet can stay happy. (Boots like the Justin Stampede tick all the boxes!)

7 Most Comfortable Cowgirl Boots: 

Want to see even more options? Check out our 16 Best Cowboy Boots and the 10 Best Men’s Cowboy Boots.

Justin Stampede Boot

This brand’s “Built for Performance and Style” motto is alive and well in their Stampede boot. Fashionable enough for happy hour and functional enough for the cow pens, Justin offers the truly all-purpose cowgirl boot you’ve been looking for.

Cushioned with a roomy toe helps you meet the demands of your day without sore feet.

Click to see this boot on Amazon

What’s to Love?

  • J-flex comfort system and rubber sole are designed to last for years
  • Removable orthotic inserts distribute impact
  • Square toe keeps your little piggies from getting pinched
  • Stabilization technology provides superior support
  • Built for long-term durability

Read Customer Reviews on AmazonReturn to boot list

Corral Heart Angel Wing

If you’re looking for a more free-spirit design, the Corral Heart Angel boot pairs perfectly with a cute western dress.

Heading out on the dance floor? This boot is a great option for dancing all night.

Click to see this boot on Amazon

What’s to love?

  • Well-cushioned insoles keep you comfortable all day
  • Goatskin leather feels soft and supple (read: no long break-in period)
  • Intricate design dresses up or down easily

Read Customer Reviews on AmazonReturn to boot list

Once you pick your perfect pair, check out the 10 Fashion-Forward Western Dresses to Wear with Boots.

Laredo Miss Kate Western Boot

Sometimes you want the comfort and design of a classic western boot, but with a little extra pizazz. The Laredo Miss Kate boot helps you feel like you’re wearing your daily ranch footwear — without looking like it.

If you’re also a horse rider, you’ll love how easily this boots can go from the corral to your favorite bar.

Click to see this western cowboy boot on Amazon

What’s to love?

  • Cushioned insole protects your footbed all day
  • Flexible and durable outsole moves with your feet
  • Pull tabs allow for easy on/off
  • Rustic saddle brown and dusty blue design looks great with jeans

Read Customer Reviews on AmazonReturn to boot list

Ariat Fat Baby Heritage

Ladies with wide feet often struggle to find comfortable boots. That struggle ends with the Ariat Fat Baby Heritage Boot. Not only can you choose from a wide variety of colors and patterns, your feet will have plenty of room to breathe.

This leather boot is beloved for taking virtually no time to break in.

Click to see this western cowboy boot at Amazon

What’s to love?

  • Durable rubber sole mitigates wear and tear
  • 4LR foot support system cushions your feet
  • Contains four comfy layers of soft footbed
  • The lightweight full-grain leather shank increases stabilization
  • A favorite among equestrians with beautiful stitching

Read Customer Reviews on AmazonReturn to boot list

See why the Fat Baby made our list of the 12 Most Comfortable Cowboy Boots for Walking.

Teva De La Vina

Tall cowgirl boots aren’t everyone’s cup of tea, so we’re excited to feature the Teva De La Vina fashion boot on our list. Not quite an ankle boot, this low boot has a subtle and versatile design and pairs with any outfit.

Not all western boots have to look…well, western. 

Click to see this fashion boot at Amazon

What’s to love?

  • Waterproof 100% leather exterior holds up the elements
  • Side zipper, adjustable ankle strap, and pull-on back loop are quite handy
  • Mush® Infused insole offers long-lasting comfort
  • Spider365 Rubber outsole ensures top traction and durability
  • Equestrian-inspired design is cute and versatile

Read Customer Reviews on AmazonReturn to boot list

Love fashion? Us, too! Check out 20 Fashionista Tips: How to Wear Cowboy Boots in the Summer.

online horse courses

Roper Riley Western Boot

The Roper Riley boot is stylish, comfortable, and an affordable choice. If you only wear cowgirl boots from time to time, this riding boot is all you’ll need in your closet.

This boot comes in a variety of colors and beautiful stitching so you can match your favorite outfits.

Click to see this riding boot at Amazon

What’s to love?

  • Padded footbed is suitable for all-day wear
  • Quality craftsmanship
  • Breathable leather lining
  • Lightweight rubber outsole
  • Pull tabs for easy on/off

Read Customer Reviews on Amazon

Chisos No. 3

Handcrafted in Texas, the Chisos No. 3 boasts unmatched comfort with an elegant finish. Traditional construction meets modern day technology (Comfort Insole System) in this luxury boot.

Chisos’ unique tanning process makes the leather incredibly soft with no break-in period.

Chisos #3 Cowboy Boot

Click to see this boot at Chisos

They’re also ethically made in a small shop using only retired dairy cowhide (read: no calfskin).

What’s to love?

  • Comfort Insole System feels more like a tennis shoe
  • Traditional handcrafted boots with pointed toe
  • 100% full leather heel counter
  • Soft leather (no breaking in)
  • Incredible durability

Read More About ChisosReturn to boot list

Parting Thoughts

We’ve given you a head start on your search, but there are many more options available. It’s possible to have both comfort and fashion, and you deserve both in your perfect boot.

P.S. Enjoy this article? Trot on over to:

online horse courses
Love it? Share it!

About the author

Horse Rookie

I began riding horses at age six, and I'm just as infatuated (OK, more!) with the sport decades later. My AQHA gelding exemplifies the versatility of the breed -- reined cow horse, reining, roping, ranch riding, trail, dressage, and jumping. We're also dipping our toes (hooves) into Working Equitation!