“What we believe first and foremost with a cowboy boot is that it [must] follow the traditional standards for construction,” Will Ormes tells me, with an accent so strong he has to be a born-and-bred Texan. A few minutes ago, he tipped his black Stetson in greeting and sat down across from me at the hat-room bar at Allens Boots in Austin. The first sign that you’re in a solid boot-shopping establishment: chivalry is alive and well.

Ormes, a manager at Allens, has agreed to give me a history lesson on a cowboy or cowgirl’s most prized possession: a pair of trusty, worn-in leather boots. He explains how stacked leather and a stainless steel shank, a thin bar most often found in work boots that adds additional stability between the outsole and the footbed, are preferably paired with lemonwood pegs that  marry the insole and the outsole (though brass tacks will make for a more affordable option). He shares his grandfather’s “old-fashioned” advice on molding a new pair of boots (“Put on your boot and go stand in the crick”). He emphasizes the importance of the “beautiful, handcrafted goods” that come together to make each boot. If the boots are made right, they should last “a really long time,” says Ormes, depending on what you’re using them for (the official Texanist ruling from my colleague David Courtney is that “there’s no expiration date”), which means plenty of pairs end up with more than one owner over a lifetime.

The second way to know you’ve wandered into a reputable boot shop: the smell. The sweet and distinct scent of fresh leather is intoxicating, so much so that there are candles that try to replicate the smell. Ask most any Texan, and they’ll be familiar. More often than not, the smell is a telltale sign of authenticity. It’s how you know you’ve hit the jackpot, and I’m all about winning the thrift lottery, whether that means finding your perfect pair of used cowboy boots sitting atop your grandmother’s old wooden dresser or under piles of stained clothing in a vintage shop. 

The benefits of thrift shopping instead of buying new have always been great deals, discounted prices, and choosing a more sustainable option. Margaret Walker, one half of the San Antonio–based bootmaking-sister duo Fraulein, is well-versed in the importance of a comfortable boot. Her number one rule for finding a worthy pair: look for solid, handmade materials. “If it’s already an old boot and you don’t get good materials, it’s not going to last,” Walker says. “If it hasn’t been used very much, there might be a reason for it. As far as comfort is concerned, I learned that the hard way.”

Below, you’ll find a list of things to remember while perusing used and refurbished boots. Oh, and don’t forget to bring a pair of thick socks along with you.

Soles, Sizing, and Pull Straps

The first sign of wear and tear will be displayed at the bottom of the boot, known as the sole. It’s normal for soles to be scuffed up, but if the bottoms seem as though they’ve seen a few too many dance halls in their day, you may want to take this pair to a cobbler. 

No matter whether you’re buying old or new, the fit of a cowboy boot is the most important consideration. You could have in your hand the finest ostrich-leather boots for an unbeatable price, but if they’re a little off your size, you’ll regret it. Ormes recommends you “take your shoe size and go down a half size.” The boot should feel snug in the middle of your foot, where your arch is. It’s a common mistake to want your boot to have some room for your foot to breathe. Fight that urge—you want the boot to be hugging you. The leather will still find a way to mold to your foot even if the boot is vintage, says Ormes. If your boot is too loose, it could slip off right in the middle of a high kick.

Always check the pull straps, the extra bits of fabric looped at the top of your boot. Often one of the most worn parts of a boot, the pull straps are used to pull the boot onto your foot. Because you want the insole to be snug, the pull straps are one of the greatest inventions for pulling the hell out of your shoe (followed closely by the bootjack, a tool for getting your kicks back off). When you’re buying secondhand, the pull straps can be frayed and thin. Nothing a cobbler can’t fix, but if you want to wear boots right off the rack to that Bad Bunny concert you’re going to later that night, you’ll want pull straps that hold even after the tightest tug. 

The Heel Test

When I bought my first patent leather heeled boots, just two years ago, manager Ray B. Calderon at Allens was the man who helped me. He was so knowledgeable about the way a boot is supposed to feel and fit, he could’ve convinced me to get a size I’d never tried (which he did, and I bought—a half size smaller than usual). The following golden nugget of wisdom may be the most important part of this guide: “When you step on the ball of your foot and move your heel up and down, [your heel] should move a quarter inch,” Calderon says. 

Circling back to said patent leather boots, I was having trouble getting them to give my foot a little bit of room. Calderon suggested taking a boot tree lathered with boot conditioner and placing it inside the boot, to stretch the instep. There’s not much that boot conditioner—a boot’s version of skin moisturizer—can’t fix. “A lotta condition and a lotta love,” Calderon says. 

As for a tip for breaking your boots in the fastest, Ormes suggests wearing them 24/7. “When I say wear them, I mean wear them for three days straight. Take it off for bed if you want, but I highly recommend you wear them for three days straight.”

The Inevitable Imperfection 

According to Ormes, “a traditional cowboy boot is going to take well over a month to break in fully and feel comfortable.” With a thrifted or refurbished boot, you may spot the opposite problem—boots that seem too worn out to wear.  But there’s a fix for that.  

“You can take it to a reputable cobbler, and you can get a new leather bottom sewn on it. That boot at that point will start its life as a new boot, despite minor finishing and wear to it,” Ormes says. “It’s a great process. As cowboys, we believe that you should get a product that will last you through any condition, no matter what.” 

While these rules and guidelines may help you find a great pair of cowboy boots, I am all too familiar with the unexpected. Say you find a pair that makes your heart pitter-patter, but there’s a bit of a tear on the shaft. The solution: bling. Houston-based Carla Valencia Design uses “old-world embroidery techniques passed down by the women in [Valencia’s] family to create modern designs using . . . symbols and icons” such as stars and angel wings, along with lettering and personalized embroidery, in lots of bright colors. 

What They’ll Cost You

For secondhand boots that aren’t touting a big-name brand, you’re likely to find prices in the $40–$60 range. Lightly worn boots from major names such as Tecovas, Tony Lama, and Lucchese will cost you in the $200 range, depending on their condition—though Ormes recommends that if you find a pair of Luccheses in your size, you buy them no matter what. “[It’s] well over one-hundred-fifty years of American legacy built into one boot,” he says. “It is the cowboy boot. It has been from the beginning, [and] it still is now.”

Cowboy boots are durable, come in many shapes and toe styles, and are a great addition to most any outfit. No matter where you find ’em or how much you pay, investing in a pair of well-made boots is a win. When you slip your cowboy boots on, you’re not just wearing shoes. You’re wearing history.