The humble, hardworking cowboy of the 1800s would undoubtedly be surprised to learn that his everyday work boots are now fashion statements. Everything about the original cowboy boot was based on function, not fashion.

The pointy tip was designed to make it easier for the cowpokes to insert their boots into stirrups. While flat-front boots required perfect aim, the pointy tip helped ease the boot into the stirrup without requiring much precision.

The heel wasn’t designed to make diminutive cowboys feel taller; its purpose was to make it easier to rest the boot on the stirrup for hours at a time.

When the cowboy was working with livestock off the horse, the heel served as a kind of brake he could dig into the ground, to prevent ornery cows from pulling him around by his rope.

Similarly, the high shaft of the boot protected the cowboy’s legs from brambles, barbed wired, snakes and blunt-force trauma.

Common Mistakes to Avoid and Sizing Tips

First, make sure you have a clear idea of why you’re buying cowboy boots.

Is it to wear at the rodeo once a year, for a country-and-western dance class, or are you considering taking up riding horses as a hobby?

  • Riding boots need to come up higher to protect the legs as they bounce against the horse and various leather accoutrements.
  • Since sizing can be tricky, it’s helpful to find a knowledgeable salesperson to help you. A little slippage in the heel is normal and will diminish over time. It should require a little effort to get your foot into the boot.

You should feel firm contact with insole and arch support. Your toes should have a little wiggle room but not much. If your foot just slides right it in, the boot is probably too large.

  • Make sure you wear a sock of the same style and thickness that you would normally wear.

Cowboy boots vary in width from the narrow AAA to the extra-wide EEE. Again, it’s helpful to have an expert check to see that you have enough room in the boot along the sides.

  • Another sizing tip is to squeeze the leather on the front of the boot at the turning point between the foot and the ankle. You should be able to hold a small amount of leather between your fingertips; if you can’t grab any leather, then the boot is probably too tight.

If you opt for the classic pointy-style boot, of course, the shoe will look a little long since your toes can’t squeeze themselves all the way up into the pointy part. Round-toed boots are also available, and they may be more suitable for people with wide feet.

Top Boot Brands

First-time boot shoppers may be overwhelmed by the sheer number of brands available. Most experts agree that the top brands in terms of style and value are Lucchese, Tony Lama, Ariat, Anderson Bean, Dan Post, and Nocona.

While most traditional boots are made from cow leather, there are now boots available in everything from lizard skin to ostrich skin. These skins offer a unique look and feel, but no material can beat cow leather when it comes to long-term comfort and durability.

The exotic materials tend to be prone to drying out and cracking. If you’re in the market for alligator boots, keep in mind that you’ll need to do considerably more maintenance to keep them in tip-top condition.

Cow leather also requires upkeep, but it can withstand periods of neglect without any permanent damage. 

As with any shoe, make sure you walk around the store for a while to assess how comfortable the boots are when you’re in motion. While the fit will change slightly over time, an extended break-in period should not be required.

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In 1983, I spent a year in Austin, filming Blood Simple with the Coen brothers. For a Jewish kid from Washington Heights, New York, that was an exotic locale.

From the day I arrived in Texas until the present, I have embraced all things Cowboy. This is particularly distressing to Sweetie (the wife), since she grew up outside of Fort Worth and has made it her business to disentangle herself from almost all things Cowboy.

Except for the occasional pair of fluorescent Nikes, you’ll never see my feet bound by anything other than cowboy boots. They’re comfortable, they make you an inch taller, and they embrace affectation.

 I have a dozen pairs, from Lucchese, Billy Martin, and the Bounty Hunter of Telluride, Colorado (the same place that makes my cowboy hats). I’ve got boots made of boa, distressed sheep (the boot maker’s description, not mine), leather, and ostrich.

The most indestructible ones I own are made of stingray. I also have a pair of Vibram-soled kickers for the big winter snows.

Here’s how to make a statement in cowboy boots: Focus on the lower half of the boot. It’s a shame and a temptation to have cool cactuses and longhorns fashioned out of fur on the upper half. You find yourself wondering if you can tuck your pants inside the boot.

You can’t. So let your boots make a statement where they can be seen. My advice for your first pair of boots is to go with the textured pearlescent stingray. They’re distinctive, and they make an excellent conversation piece.

I’ve owned three pairs of Billy Martin stingrays (black, blue, and green) for close to 20 years. With the exception of replacing soles and heels, they haven’t been pampered at all, not even a shine. (You don’t shine stingray; it’s part of the appeal.)

The front end of the Billy Martins comes to a point a good half inch beyond the end of the sole — very similar to a Formula One race car. One warning about the rays: You really need to fit them perfectly.

The skin is so tough that they can’t be stretched.