This Is Weird: I Want a Pair of Cowboy Boots

Pair these with your cowboy crotch.

Three things at the Jackson Hole airport made me re-think everything I know. First there were the Rocky Mountains, because where have they been my whole life? Then there was the bearded man in a pair of navy, white and yellow-striped A-line shorts that fastened right around his waist and over a flannel, all of which was merely the cake portion of his upside-down pastry of sartorial greatness. The icing: his combination of thick camp socks worn up to his calves with Tevas. (Remember that he is only second on this list.) Number three: there were so many cowboy boots being worn in earnest that I did not know what to do with myself.

I am not unfamiliar with cowboy boots. In high school I caught a few country concerts and watched barrel races at The Cow Palace, a venue too often left off of San Francisco itineraries . When the PBR Rodeo comes to Madison Square Garden in New York City each year, I go. In these contexts, the carved leather boots are extremely literal. For some, they are supposed to be: if you’re stomping around in manure and mud or need your feet to rest safely in stirrups (ahem, JoJo), cowboy boots are sturdy and practical. For others, they’re for getting into the western theme. And perhaps like country music, you either love them… or you vehemently don’t.

But in Jackson Hole, which is absolutely a western castle for authentic cowboys, horses and cattle, there were also a lot east coasters. Men and women in suits landing from Manhattan, briefcases still in hand, mixed with the happy welcoming committees who were already settled in. There were cable knit sweaters worn over shoulders, 1980s Patagonia fleeces, silk blouses, kilim textiles and every take on denim that you could imagine. Save for the Teva man, these cowboy boots seemed to pair with just about everything. Maybe that’s because no one was wearing a theme; everyone was just existing.

Ahh!! And everyone looked so cool!

Ever since I landed back in Manhattan I’ve been wondering if I, too, can do the cowboy boot. I borrowed a red pair from Ariat to play around with in my closet and what I am learning is that because this isn’t a look that’s particularly authentic to me — or, at the very least, it doesn’t come naturally — there’s still some trial and error to be had. But here’s what I’ve determined:

They definitely do not work with everything. They’re a challenge.

It’s easy to go too literal, too costume-y, too quickly.

Likewise, veering too far away from the western roots on purpose somehow looks just as fake.

But while sifting through various references in the Rolodex of my brain, I remembered Matthew McConaughey in Dazed and Confused and tried to channel him: laid-back, relaxed. Kind of creepy. Yeah. But cool. He made the boots look like his feet knew no other shoes.

So the cowboy key is to dress naturally, somewhat casually, and personally, I prefer a straight leg (as opposed to skinny, flared or bootcut) jean. You can’t overthink it but you do have to be strategic. And confident. Like cattle, I think these boots can smell fear.


Photographed by Krista Anna Lewis; Ariat boots featured throughout.


Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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