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Unless you were born and raised on a ranch, cowboy boots can be notoriously difficult for the average guy to pull off without looking like a (rodeo) clown. But that doesn’t mean you shouldn’t try, especially since they’ve become a menswear must-have.
“It’s no longer cattlemen and ranch hands picking up the boots, but fashion-savvy guys wearing them on the streets of New York, Paris, and everywhere in between,” New York City-based fashion stylist Seppe Tirabassi tells Men’s Journal. “At the moment it’s very on-trend, but it will always remain a timeless footwear staple rooted in genuine American craftsmanship.”
Not all Western-style boots fit inside the cowboy category—they’ve got to tick a few boxes that help their wearers be saddle-ready, per their original purpose. True cowboy boots come with a rounded or pointed toe, originally designed to help the foot enter a stirrup. They also must have a Cuban heel (the fancy name for a straight, medium-high heel with a slightly curved back), which keeps the shoe secure once it’s in the stirrup. Cowboy boots have a high shaft that makes them easy to pull on, and you’ll never ever see laces or any other embellishment that could get caught on something while riding a horse. Lastly, they’re always constructed with durable material—mostly tough leather—that can protect the wearer’s feet from brushes with barbed wire, animals, dust, dirt, and all kinds of other obstacles a cowboy might face.
One variation on the classic cowboy boot is the roper. It’s essentially a streamlined modern version of the cowboy boot with a lower heel and shorter shaft. It was created for steer wrestlers at the rodeo who needed to run faster on foot. No matter what style you choose, however, cowboy boots are timeless—and they get better with age.
“Cowboy boots are an iconic piece of the Americana wardrobe that are made to last a lifetime,” Tirabassi says. “And the more beat-up they look, the cooler they are. Second-hand boots can command even higher prices since customers are really going after the worn-in appeal.”
Below, Tirabassi picked 11 pairs of cowboy boots from his favorite bootmakers and recommended foolproof ways to style them. Time to saddle up.
Named after the legendary racehorse Secretariat, Ariat integrates athletic footwear technology into its equestrian boots, which are among the most supremely comfortable and stylish on the market.
“The contrast between the leather and traditional stitching is a great detail on this particular boot,” Tirabassi says. “Go for a black-on-black look with slim black jeans that you can tuck into the boot so the artistic stitching really stands out. Throw on a leather jacket and you’re good to go.”
Justin Boot Company has expertly crafted authentic Western footwear in the United States since 1879.
“These guys are the original makers of the modern-day roper cowboy boot,” says Tirabassi. “The heel here is a little higher than what you’d normally see on a roper, but that just means you’ll stand a little taller and prouder. I like the smooth black leather because it can go with just about anything in your wardrobe, even a wool suit.”
Old Gringo’s handcrafted boots are known for featuring beautiful embroidery while also staying true to the roots of Western style. To get more use out of your boot, Tirabassi recommends investing in a simpler style with understated details.
“The distressed leather is a great look and the harness detail gives the boot even more of an edge,” he says. “Pair it with a worn-in light wash or vintage jeans and a white tee. You’ll fit right in whether you’re on a Texas ranch or Sunset Boulevard in L.A.”
The Frye Company has been in the boot biz for over 150 years, and it has developed a loyal following for its signature designs that stand the test of time.
“These Fryes are versatile since there’s no flashy stitching, and they’re super comfortable since the round toe won’t cramp your feet,” says Tirabassi. “For this pair, you can pull your dark denim pants over the boot instead of tucking them inside.”
It takes over 200 steps to make a single Tecovas boot, and each one is crafted by hand in León, Mexico. Tecovas boots are known for their incredibly supple exotic leathers—from python to crocodile—as well as for their intricate stitch designs.
“If there’s one high-end pair to splurge on, it’s these Tecovas made from Nile crocodile,” Tirabassi says. “Don’t go stomping around the rodeo in this pair—show off your Marshalls when you’re dressing to impress at an upscale restaurant or fancy wedding.”
The Lucchese brothers came to America from Italy in 1882, and opened their first bootmaking shop in San Antonio, TX the following year. Lucchese boots have a reputation for superior quality and are often gifted to dignitaries around the world. Tirabassi appreciates the heel height on these boots and their unique material.
“I love how suede wears in over the years, and there’s a softness to how they look and feel,” he says. “The suede, combined with the sleeker silhouette, also gives the shoes a more modern appearance.”
He also recommends pairing them with some accessories from Peyote Bird, one of his favorite artisan jewelry brands.
Another boot company with Italian origins, Ferrini is known for making surprisingly affordable boots with exotic leathers like ostrich.
“Full quill ostrich is the most coveted type of ostrich leather, instantly recognizable with a bumpy look and feel,” Tirabassi says. “Half ostrich or smooth ostrich shows less of a quill pattern, and leather from the ostrich’s leg looks more scaly, almost reptilian.”
Durango boots combine traditional styles with modern tech like waterproofing and tough-as-nails rubber soles to prevent slippage and keep your feet comfortable.
“This pair of Durangos is the best bang for your buck,” Tirabassi says. “It’s a classic square-toe cowboy boot that won’t break the bank, with added features for comfort like a non-slip rubber outsole instead of typical leather bottoms, plus memory foam in the footbed.”
The affordable price points of Laredo boots make them among the most popular choices for Western-style boots.
“The metal details at the toe and heel add a nice flair to your typical black leather cowboy boots,” says Tirabassi. “Go for James Dean vibes when you complete the look with a white tee, black jeans, and a black leather jacket with metal hardware.”
Tony Lama, the son of Italian immigrants, started learning the boot trade from his uncle at the tender age of 11. He eventually became a cobbler for the U.S. Cavalry at Fort Bliss, and in 1911, founded his eponymous boot shop in El Paso, TX. Tony Lama remained family-owned until 1990, when it was purchased by Justin Brands, but it still makes great boots.
“These are your classic chocolate leather boots that will age super well—in five years, they’ll look like gold and everyone will be asking where you got them,” says Tirabassi.
Mexican-born and Texas-bred, Rios of Mercedes has been making some of the world’s finest cowboy boots with artist-like devotion since 1853. The brand continues to earn endorsements from famed musicians and performance-horse greats alike.
“Planet Cowboy in Nashville should be your go-to for anything cowboy-related, including this pair of boots from Rios of Mercedes,” says Tirabassi. “I love the pointy toe and warm burgundy color because it’s different from the rest of the pack, but still not too loud or in-your-face. The waxed leather gives it a vintage look that completes any fall or winter outfit.”