ask a cool person

What Are the Best Cowboy Boots?

Photo: Courtesy of MGM Cartoons

Step into a pair of cowboy boots and something magic happens: Your weight shifts, you pop one hip out to the side, and suddenly the jeans (or yoga pants) you were wearing become an actual outfit. And if they’re good cowboy boots, they’ll be comfortable too. With all of the cowboy (and cowboy-inspired) boots to choose from online — and everyone from Everlane to Isabel Marant offering their take on the Western trend — it can be hard to know which ones are right for you. To help you decide, we asked a wide range of stylish experts — from real-life cowgirls and country singers to stylish teens and women who work in fashion — about their favorite cowboy boots to wear to the office, on horseback, and even onstage.

Of the 12 women we spoke with, four praised these boots from Ariat. Singer-songwriter Frankie Zwick, who spends winters in Nashville and has worked as a wrangler for five seasons on ranches in Wyoming and Colorado, says: “I pretty much wear one pair of Ariat boots. A lot of the girls I’ve worked with throughout the years wear them, too. The boots have rubber soles, so if you’re riding or working in the mud, they’re gonna hold up really well.” Zwick wears her distressed-brown Ariats everywhere and likes that she can go from working on a ranch straight to a Honky Tonk in Nashville without having to change her footwear. She says they stand up well to spilled drinks and getting your toes stepped on.

Other fans of Ariat include Amalie MacGowan, social media manager at Man Repeller, writer Jessie Mooney, rodeo barrel racer Keiara Monique, and Nicole Zuelke, a model, actress, and avid horseback rider. MacGowan likes Ariats as an affordable alternative to higher-end designer pairs. (She also owns a few boots from Ganni and a handmade pair from Brother Vellies). She says Ariat has a ton of great options between $100–$200, all with a genuine cowboy boot look and feel. “If you’re gonna do cowboy, you might as well do it full hog,” she says. Mooney bought her pair of Ariat Heritage boots in Nashville in 2017 “on the recommendation of my little sister and her most Southern friend,” because they hit a sweet spot of comfort and style. Of the options she tried that day, the Ariats were the most comfortable, had a subtle-enough design to wear with lots of different outfits, and fell at just the right place on her calf to keep her from looking “stumpy.” Monique, who lives in Los Angeles and has been riding horses since she was 8 months old, wears her Ariats both in and out of the saddle. She says they’re by far the most comfortable boots she’s worn and tells us her 3-year-old daughter wears them, too. “I had a pair of Justin boots that were okay,” she says. “But after a while, they’d start to hurt my feet. Whereas I can wear Ariats for over 12 hours. I might be tired, but my feet don’t hurt. They are just cushier.”

Five of the women we spoke to mentioned wearing Frye boots, whether it was a vintage pair they’ve owned for over a decade or a new pair they’re still breaking in. MacGowan’s Frye boots, which she bought three years ago, are shorter and less traditional than Ariats, but their heel and snip toe make them still feel sufficiently Western. She says they’ve aged “like a fine wine” and that she often wears them on planes — a testament to how comfortable they are. Musician Courtney Marie Andrews, who’s owned many Frye boots, wears the Frye Western Chelsea boots almost every day. “Once you wear them in, they form to your foot and are extremely comfortable,” she says. They also look great with a cropped pair of jeans.

Devine Blacksher, fashion assistant at the Cut, describes her Frye boots as supercomfortable and high-quality. “I probably wear them three to four times a week, to work and going out at night,” she says. For weekend errands, she’ll often throw them on with yoga pants.

Lucchese boots have set the industry standard for craftsmanship and design for over a hundred years. The company offers a huge variety of styles, from highly decorative boots you’d wear onstage to less flashy pairs you could wear to muck stalls. Molly Bedell, founder of Two Old Hippies boutique in Nashville, has a pair of Lucchese boots that were custom-made to her foot, which she says is “the way to do” it, if you can. The non-bespoke options are excellent too, says Zuelke, who wears only Lucchese boots. She likes them for their durability and range of designs. Although the brand is mainly known for its dress boots, Lucchese does make a barn boot, which Zuelke wears whenever she rides. “I’d say I’m on a horse four to five days a week. I wear the barn boots in the snow, the mud, even through muck and manure, and they hold up really well.” Like the Ariat boots above, these barn boots have rubber soles, which adds to their comfort and keeps out moisture. Zuelke also wears a pair of patent leather knee-high boots called the Priscilla that she saves for nights out — and that she says get her compliments all the time. And although she spends most of her time in Ariats, Zwick has a pair of cream-colored showstopper boots from Lucchese that she wears when performing. “They’re not the kind you would ride in,” she says “but they’re really high-quality.”

Three of the women we spoke with wear Ganni cowboy boots on a regular basis, noting that they are both comfortable and go with everything. MacGowan has two pairs — white ankle boots and a wilder pink-and-black pair with star cutouts and rhinestone detailing. The white boots “have gotten the most mileage, by far,” she says. “They have some scuffs, because it’s impossible to keep a white boot pristine, but the wear gives them character.” Chloe, a stylish 18-year-old with more than 20,000 followers on Instagram, says her black Ganni cowboy boots with star cutouts and white stitching are now a part of her daily uniform. “Cowboy boots have become pretty ubiquitous over the past few months, but I love Ganni’s modern, more structured take on them,” she says. And Christel Langué, a personal shopper and stylist, tells us that her Ganni boots are supercomfortable and get lots of compliments, including on her recent trip to the Sundance Film Festival in Park City. “I truly never travel without them,” she says. Ganni’s boots go with everything, she says.

If you’re looking to find cowboy boots for under $100 dollars, Strategist writer Lauren Ro says this pair of Durango Western booties have held up well throughout years of wear and that they go well with everything from jeans to tights and a skirt. “They are supercomfortable, and the little heel makes a big difference,” she says. Ro loves the sleek low-top boots so much she recently took them to a cobbler to be resoled.

Several of the women we interviewed said either they owned a pair of Old Gringo boots or wanted to own a pair. Bedell recommends these made-in-America boots for their incredible embroidery and the variety of heel heights and toe styles. Andrews also likes their unique designs. “I wear cowboy boots for style and originality, so if I were to shop for a fun and storytelling boot, I’d search for a fun pair of Old Gringos,” she says.

Of course, if you’re looking to go headlong into the current trend and literally walk a mile in a pair worn by Lil Nas X, you could get these handmade pony-hide Western boots from Los Angeles designer PS Kaufman. Molly Salvi, owner of Squash Blossom Vintage, is a fan of the brand for their modern spin on traditional cowboy boots made with superfine leather and a Cuban heel. “They’re the boots that get me stopped every time I wear them,” she says. They’re immediately comfortable, too: She walked miles and miles around Los Angeles the day she got them, and they didn’t take anything to break in.

The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.

What Are the Best Cowboy Boots?