The humble cowboy hat, iconic though it may be, had simple origins. Philadelphia-based hatmaker John Batterson Stetson—that last name ought to be familiar—released, back in 1865, the “Boss of the Plains” hat, intended to cater to the needs of folks who spent their days on horseback under the hot sun. It didn’t look much like what we’d call a cowboy hat today. Its crown was high, smooth, and uncreased, and its brim was wide and flat. It did its job, though, more or less, providing coverage from the sun and, being waterproof, from the rain. Even then, the hats weren’t cheap—at five dollars for the most basic version, buying a Stetson in 1865 was the equivalent of sinking a hundred bucks into your hat today.
Over time, the hat evolved both in form and function. It did so for two reasons. One was practical—the brim became upturned on the sides to keep it from interfering with a rope, and the crown was pinched to allow for easy removal, allowing it to compete with the more popular bowler hats frequently worn on the plains. The other was fashion, as Wild West shows and later Hollywood used the hat to create a simple iconography to denote who was a cowboy, and thus a hero.
From there, the cowboy hat has remained more or less unchanged. It’s practical enough to wear while doing ranch work and stylish enough to wear on the town, and it still carries the connotations that have made it a favorite of everyone from Willie Nelson to Lil Nas X to Megan Thee Stallion. Conjure an image in your mind’s eye of a country singer, and tell us what’s on his head as he croons into the microphone.
Now do the same for Amazon founder Jeff Bezos.
If you have an idea of what the 59-year-old third-richest man in the world looks like, you’re probably picturing his bald dome, maybe adorned with a ball cap with a logo for, say, Blue Origin—his rocket company with a launch site in far West Texas—or the ubiquitous Amazon “smile” logo. But when a man like Bezos wants to show his “authentic” side, those hats simply don’t do the job, as we learned when Bezos posed for a Vogue magazine photo shoot with his fiancée, Lauren Sánchez. In the shoot’s most memorable photo, Bezos sits, Sánchez draped over him, in the cab of a vintage yellow van, presumably in some part of the vast stretch of West Texas land he owns (Blue Origin’s spaceport is located just outside the small town of Van Horn). Sánchez, the caption notes, wears a Levi’s tank top, while the tech billionaire, clearly fresh from doing a set of push-ups to pump his improbably jacked biceps, wears a dark T-shirt, blue jeans, some wrist jewelry, and a black cowboy hat as he gives the camera the vaguest hint of a smile.
Why is Bezos wearing this ten-gallon hat in Vogue? It’s not because he was reminded of the photo shoot at the last minute, wrangled to the vehicle by an assistant while he was out roping cattle. The article notes that Bezos did spend time in Texas as a boy—his grandfather owned land in Cotulla, a small town (with a vastly different landscape from Bezos’s chunk of West Texas) midway between Laredo and San Antonio—but it seems obvious that he’s focused on the semiotics here. This isn’t even the first time Bezos has been photographed in a cowboy hat—he tried a similar gambit in 2021, at a press conference after a Blue Origin launch, when he inexplicably chatted with reporters in a hat that attracted more attention than the fact that he’d just worn it to space. Bezos wears the cowboy hat for the same reason that, say, Kid Rock (the son of a car-dealership owner from the Detroit exurbs) and George W. Bush (the son of a politician from Connecticut) have always loved to be photographed in one—because it suggests a certain kind of down-home authenticity, evoking in the mind of the viewer others who wear cowboy hats, which is to say, good guys in movies and men who work with their hands. Can Jeff Bezos, Kid Rock, or George W. Bush lasso a steer or fix your truck if it breaks down on the side of the highway? Almost certainly not, but they’d like to look like someone who could, and the hat is a way to grab that for just a few hundred bucks.
Bezos is hardly alone in his interest in this sort of authenticity drag; indeed, Elon Musk—one of just two people on the planet with more money than Bezos, and also a part-time Texan who runs his own private space program—made headlines just a few months ago for donning a black felt cowboy hat of his own on a September trip to the border community of Eagle Pass as he decided to wade into the immigration debate. Musk live streamed his visit (or at least attempted to), but the most memorable image wasn’t the sight of Musk and San Antonio congressman Tony Gonzales (who forewent a hat of his own) chatting in front of an assembly of detained migrants; rather, it was a screenshot of Musk, in mirrored aviators, mugging for the camera in a hat that looked so strange upon his noggin that observers thought he might have been wearing it backwards. Mark Harris, managing director of Stetson London, noted that the buckle was on the left, which would indicate a hat worn correctly—but if you need a professional hatmaker to affirm that you’re not wearing your hat backwards, you’ve already lost.
Recognizing the potential for his cowboy cosplay to have the opposite effect of what Musk intended, the SpaceX and Tesla CEO took to X to affirm that his outfit wasn’t something he picked up on the way to Eagle Pass, noting, “Just for the record, my boots are 20 years old and my hat is ten years old.” In other words, Musk didn’t just wear a hat that made him look like a dork that day, he’s been wearing a hat that makes him look like a dork for a decade; thanks for clearing that up.
But ultimately, the true subtext of the cowboy-hat-as-symbol-of-authenticity that Bezos, Musk, and most others are trying to tap into is that they’re just trying too hard. Sometimes a cowboy is just a man in a cowboy suit, as the musician John Vanderslice once sang, and the authenticity these men crave is, paradoxically, the one thing that even a fortune the size of Musk’s or Bezos’s can’t buy.