It’s been almost 20 years since I bought my first pair of cowboy boots. I had just graduated high school, looking for something more durable than the sneakers I was tearing through every six months. I didn’t know much about boots at the time, I just knew they looked cool, had a reputation for lasting a long time, and could be resoled. So, I took the plunge and picked up a pair of Boulet 7031s.
I wore them everywhere. Through mud, snow, gigs, road trips, you name it. They’ve been resoled seven times, had their welt replaced, heel caps swapped out more times than I can count, and they’re still going. But with nearly two decades of boot experience behind me, there are three big things I wish I had known before I got those first boots. And if I could do it all over again, I’d definitely take a different approach.
Here’s what I’ve learned, and what every first-time cowboy boot buyer should know.
1. Get the Right Size the First Time
This one sounds obvious, but it’s the most common mistake and the one that caused me the most pain. Literally.
When I bought my first pair, I didn’t really know my true cowboy boot size. I ended up in a pair that was too short. Sure, the width felt okay, but the length wasn’t right. I wore them anyway (because, hey, I loved them!), but they were a nightmare to break in. I still have calluses on my toes from where the leather pressed too tight. And you can actually see the bulge where my foot pushed out the side of the boot.
I later found out that I’m a 12B, a narrow width that’s hard to find these days. A lot of stores just don’t carry narrow sizes anymore, and many salespeople will try to fit you into something close, saying, “This should work fine.” Trust me... don’t settle. If the size isn’t right, walk away.
Use a Brannock device (that metal foot-measuring tool in most shoe stores) and get your true size: length and width. Boot makers are supposed to size according to Brannock measurements, so if you’re a 12B, don’t let someone talk you into an 11D. That’s not going to feel good long-term, and it defeats the whole purpose of investing in a quality pair of boots.
2. Know How Fast Leather Soles Wear Down
One of the reasons I was drawn to cowboy boots was their repairability. I loved the idea of buying something once and keeping it for decades. But what I didn’t realize was how fast leather soles can wear out, especially if you wear them every day.
If you’re walking on pavement, concrete, or rough terrain daily, you might burn through a leather outsole in 6 to 12 months. Same goes for rubber heel caps, they wear down quickly under consistent use.
The trick here is to either:
- Add sole savers (a thin layer of rubber that protects the leather outsole),
- Start a rotation with multiple pairs of boots,
- Or choose a boot with a rubber outsole for more durability right out of the box.
Now, I love leather soles for their look and feel, but I’ve learned to manage my expectations. If you plan to wear your boots hard and often, think ahead about how long you want that sole to last and be ready to resole before you wear down to the insole. Once you hit the insole, repairs get expensive or even impossible.
Also, a quick word of warning for boots in the $150–$350 price range: if they have leather soles and get soaked with water early on, there’s a decent chance they’ll separate from the welt. That happens when the glue hasn’t had enough time to cure at the factory, a common shortcut when production is rushed. Once separation happens, a resole is your only hope.
3. Slightly Used Boots Are a Goldmine
If I could go back in time, I’d skip the brand-new boots and head straight for the slightly used section.
Seriously, the used boot market is one of the best-kept secrets in the Western wear world. You can find lightly worn or even virtually new cowboy boots on sites like:
- eBay
- ShopGoodwill
- Facebook Marketplace
- Vintage stores and consignment shops
I recently picked up a stunning pair of Dan Post lizard boots for just $13 on ShopGoodwill. You could still see the logo on the heel cap and they were basically brand new.
And check this out: I also scored a pair of Cristobal Romero bullhide boots, handmade in 1983 at the Don Quijote factory in Mexico, for $200 on eBay. They’re incredibly high quality and way better than any new boot I could’ve bought for that price.
The great thing about buying secondhand is that it’s low risk. If you spend $30 or $40 on a pair and the fit is a little off? No big deal. You’ve just learned more about your sizing without breaking the bank. You can even try different toe shapes, heel styles, or exotic leathers without dropping hundreds of dollars.
Buying slightly used boots helps you learn what you like—what fits your foot best and what styles you reach for again and again.
Bonus Tip: Don’t Believe the “Break-In Pain” Myth
One of the biggest myths about cowboy boots is that they’re supposed to be painful to break in. That’s just not true. Not if they fit right.
If you’re wincing every time you walk or developing blisters and calluses, the boot probably isn’t the right size or shape for your foot. A well-made, properly fitting boot should feel snug but comfortable from day one and get even better as it molds to your foot.
Final Thoughts
I still love my first pair of boots. They’ve been through a lot with me. They’re scuffed and cracked, but full of memories. But if I were to start my cowboy boot journey today, I’d do it smarter: I’d get measured properly, know how quickly certain materials wear, and dive headfirst into the secondhand market.
So if you're thinking about buying your first pair, or if you’ve already taken the plunge and want to improve your experience going forward, I hope this post helps point you in the right direction.
Thanks and step strong!