How To Find Your Cowboy Hat

[7 min read] Authenticity is a key ingredient. But how do we determine what feels right in a world brimming with alternatives?

In Santa Fe, I discovered that there are many opportunities to buy many kinds of well-crafted cowboy hats. And after a healthy plate of enchiladas “Christmas style” (with red and green chiles), returning home to New England with an authentic hat began to feel plausible…like I could really see myself wearing a cowboy hat while…I dunno…walking in my neighborhood, heading to the gym…or running an errand. It didn’t take long for the lunchtime spice hangover to dull any question of whether I should don a cowboy hat in New England, where the baseball cap and knit beanie dominate noggin apparel. I was going to bring a bit of the Southwest back East.

Stretch the Imagination

Indigestion is the mother of compromise, and I decided that a cowboy hat in Boston must be authentic to be worn with any degree of social acceptance. Authenticity is a bridge to almost anywhere. The three-point hat from revolutionary times, worn proudly while staging a battle on the town commons, is an unquestionably authentic gesture. To be fair, the hats worn in period reenactments look good for shedding rain or housing a small bird but really don’t seem poised for a comeback anytime soon. But wearing a cowboy hat every now and then shouldn’t be that big a stretch, comparatively speaking. Right?

As I walked into the Saturday farmers market, feeling slightly queasy at the sight of chile powder and ostrich eggs packed into stalls alongside greens and breads, a few questions came to mind: why do we value authenticity? And how do we choose something authentic in a place brimming with lookalikes?

Find Your Guide

My journey the next morning took me to the Santa Fe Hat Company and a fellow named JD.  He’s a warm, friendly guy with shoulder-length white hair flowing neatly from his straw cowboy hat.  JD looks like a man who has worn many hats in life, earning the horseshoes tattooed on the backs of each hand.  On hearing that I was from the East, he encouraged me to try a straw Stetson before shifting his attention to a group of new customers that had just entered the shop.  I quietly swapped it for a more traditional cowboy style.  He looked over at me again, nodded sagely, and said “Brother…I didn’t figure you for a cowboy hat but that is YOUR hat.”

I nodded graciously…and I needed a little time to think about it…so I placed the hat back on the counter and left JD to explore more of downtown in the late afternoon. Shops are nestled in low slung adobe mounds, protection from the intense Southwestern sun. After a few more tourist days filled with more chiles and enchiladas, and still without a hat, I found a competitor’s store. The door opened with a jingle, revealing dark wooden floors and hats of all kinds hanging on the walls and from racks along the ceiling.  

A woman with blond hair cascading past her waist, dressed head-to-toe in cowboy attire, arched into different poses in front of a mirror.  Nearby, two men wearing bright patriotic t-shirts and dark cowboy hats lounged and laughed across broad, leather chairs. 

I walked further into the store and pretended to study a row of custom hats starting at $800 and moseying well outside my budget.  The gents were laughing a bit louder now and a young woman approached, wearing a tight t-shirt featuring an AK-47 stretched across the American flag.  She welcomed me to the store and politely asked if I needed any help.

I politely declined and walked out of the small shop, taking a mental snapshot over my shoulder while closing the door behind me.  The young woman in her 2nd Amendment t-shirt now helping another customer, and the two patriotic onlookers smiling advice at the tall blond woman in full Western ensemble.

Wear the Narrative

My time in Sante Fe was drawing to a close and while I was still without a hat, I was a man riding with newfound purpose and intent.  My eyes took a moment to readjust to and from the afternoon sun, but I found JD where I expected, not 30 minutes before closing time.  He shared a few stories and assured me that I wasn’t buying “too much hat.”  JD made this unfortunate mistake many years ago at a bar in Missouri, narrowly escaping two real cowboys who took offense at the size of his brim.  While digging through boxes, JD talked a bit about the joy of riding a Harley and hinted at a previous scrape with The Law before confessing that “he has some issues with authority.”

I could hardly wait to pay for my new cowboy hat.

Authenticity and Trust go hand in hand, a special moment when our dreams surrounding a thing become real and possible.  Sometimes this is aided by assurances.  An authentic Rolex is certified, meets a set of standards, and we then trust it will keep time.  The other side of authenticity is the fulfillment of an emotional promise.  If I purchase an authentic Rolex, I am assured of a social standing or perception of status.

JD packed my hat gingerly to ship back East. His parting guidance was to store it upside down to protect the straw from humidity. And as I walked out of the store and into the sunset, JD nodded a final reassurance that I wasn’t buying too much brim.

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