insider goods

What to Wear to Look Like: A Cowboy

Photo: Ian Waldie/Getty Images

Status can be a funny thing. Of course, it is most obviously expressed through shiny hardware and easily recognizable logos, but it gets far more interesting when you start to observe the more subtle signals — the way you tuck your shirt, or what you eat for breakfast, or your particular brand of notebook can mark you as in or out. And, of course, what counts as a status item varies wildly across human tribes. In our series “Insider Goods,” we’re talking to members of different tribes (some with their real names, some anonymously) to learn about the niche status items among Broadway actors, ballerinas, or brain surgeons.

Today, we look to cowboys. Cowboy culture has been a fixture in popular culture for years. Recently, though, we’ve seen a spotlight on some of the intersections of western culture that have always been there but haven’t always received the attention they deserve. Over the last few years, photographer Luke Gilford published monograph National Anthem, documenting America’s queer rodeo; Netflix released Concrete Cowboy about a community of Black cowboys in Philadelphia; and Lil Nas X caused controversy as a Black artist with a chart-topping country-music hit. We reached out to Nick Villanueva, the public relations chair of the Colorado Gay Rodeo Association, and Randy Savvy, founder of the Compton Cowboys, to find out the boots, hats, and trucks popular among the cowboy community. (With the right gear, Savvy adds, “you’re a certified cowboy and nobody can tell you shit.”)

A cowboy hat

Starting with the most universally recognizable sign of cowboy — the hat. “You got the straw hat, and that’s better in the summer, it’s lighter and airier,” says Villanueva. “Then a black felt hat, and that’s mostly worn in the winter.” No matter the season, though, he likes his hat to be jeweled. “I like it to have a jeweled band or something that stands out more than just the hat,” he says. As far as brand goes, he doesn’t have a particular preference: “There’s nothing wrong with a chain, but there’s nothing better than finding that hat in some Western rural town because then there’s a story about it.” If you’re trying to get the look in the city, Villanueva says Boot Barn is a good place to go.

Savvy, who is often photographed in a black cowboy hat, says that any brimmed hat will do. “Everybody has their own vibe,” he says — and sometimes he’ll even switch out his traditional cowboy hat with a trucker cap.



For the boots, Villanueva is very particular. “I think it is debated who has the best boots, but whenever I go shopping, I like Cody James boots,” he says. He loves that they smell like leather even after “they’ve been worn a hundred times and in the dirt.” He prefers his boot with a pointed toe, he adds.

Savvy is sponsored by Ariat, so he has a lot of their gear, but he especially likes the boots. “They’re just so comfortable, they last long, and they look great,” he says. He also appreciates that the brand caters to men, women, and kids, so there’s something for the whole family.

Belt buckle

Both of our experts explained that belt buckles aren’t necessarily for everyday cowboys. Rodeo and athletic cowboys receive their buckles for competing and winning events. “You wear them as a token that you earned,” says Savvy, though you can just wear them for style. As Villanueva says, “I wouldn’t call myself a cowboy because I don’t ride, I don’t have the ranch, but you can have cowboy in your soul.” If you want to fake your championship win, there’s plenty of vintage options on Etsy.


Villanueva not only works with CGRA, but he’s also a professor at the University of Colorado, Boulder, and is writing a book on gay rodeo titled Rainbow Cattle Company — so he’s well-versed in cowboy trends of today and the past alike. One constant staple has been tight-fitting jeans. “From what I read in interviews all the way back to the 1980s, with regard to jeans, you have to have a quality-fit pair of Levi’s,” he says, and adds that Levi’s or Wrangler jeans are still what’s worn the most. In his upcoming book, there’s a quote from Guide Magazine from 1985 that gives you a clear image of the entire look: “You can’t be a real cowboy without proper accessories. You need boots. Lizard skins are the best. You need spurs. Can’t be a real cowboy without spurs on your boots. You also need a red bandana, 501 jeans, and a flannel shirt no matter how hot or humid it is. (Remember real cowboys don’t sweat.) And ideally you’ll need a horse, but realistically, a Chevy S-10 will substitute just fine.”

A flannel

Villanueva discovered the importance of a long-sleeved flannel shirt the hard way. “At my first rodeo that I was able to be behind the scenes, I had a flannel shirt on — but it was short-sleeved,” he says, and they refused to let him in. Villanueva thinks it has more to do with safety today, but loves that the quote from 1985 still holds true.



If you look on Savvy’s instagram, you’ll often see him with two forms of sun protection: a hat and sunglasses. “Out there in the beating sun or when you’re riding trail, you definitely want to be able to block the sun,” he says. He likes the look of Ray-Ban New Wayfarers the best.

A pocket knife

“It’s just a really handy thing to have in your pocket,” says Savvy of a pocket knife. “Sometimes we have to cut strings or leathers, or you need to make an extra little string to tie something up, or you have to cut the hay bale open, or anything really. Shoot, them things come in so handy, you’ll be surprised by all the different uses of them.” One from this classic brand will definitely do the trick.

A truck

Villanueva polled the cowboys and cowgirls of the CGRA before we spoke, and several mentioned the importance of a big pickup truck with a horse trailer attached. One wrote, “Roll up with your F450 dually with your four-horse slant load gooseneck that has completely decked out living quarters.”

A truck and trailer was one of the first things Savvy mentioned as well. He says a heavy-duty 4x4 pickup truck and horse trailer is mandatory as a cowboy. He’s partial to his GMC.

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What to Wear to Look Like: A Cowboy