Author: Sophie Malmon-Berg

Vintage Stetson advertisement "The Last Drop from His Stetson"

The Story of John B. Stetson



It was summer 1862. Storms were brewing over the Colorado Rockies. And when the rain hit, John B. Stetson and his colleagues went scrambling for shelter.

Thinking quickly, they fashioned coverage from the animals they had shot for food. First, a tent, which Stetson created using the felting process he had learned from his father’s business. Then, a hat. Wide-brimmed and tall-crowned, it featured a silhouette familiar today, but back then, the shape was so unusual that the other members of his party gave him grief for it. That is until a passing bullwhacker bought it from Stetson for a five-dollar gold piece.


Nearly 200 years after his birth, John B. Stetson, and the company he founded, are synonymous with innovation, independence, and handcrafted American headwear. His name appears in novels by Hemingway and Steinbeck, in iconic folk songs like “Stagger Lee,” and in more recent tunes by such varied artists as Steely Dan, The Roots, and Lyle Lovett, who sang that “My John B. Stetson was my only friend” in his classic, “Don’t Touch My Hat.

Clint Eastwood wearing a Stetson
style hat in the 1960s Western trilogy ‘The Man with No Name’.

The son of a hatter, born in 1830, the seventh of 12 children, Stetson grew up in the family business until he was diagnosed with tuberculosis while in his 20s. Seeking relief—and perhaps a bit of adventure—he headed West. He first landed in St. Joseph, Missouri, where he worked his way up the ranks of a local brickyard, becoming an owner before the factory, and his fortune washed away in a river flood. From there, he fell in with the gold rushers and cowboys of the era, making frequent expeditions to Pike’s Peak in Colorado in search of gold, which led him to that fateful Colorado rainstorm.

While in the Rockies, Stetson had noticed the shortcomings of the coonskin caps Westerners often wore. They were prone to fleas, they didn’t provide much shade from the sun, and they didn’t hold up in the rain. His invention fixed all that, and as news of this new breed of headwear took hold, Stetson headed back east to Philadelphia, launching his business in a one-room workshop with $60 he borrowed from his sister.

There, he developed The Boss of the Plains, based on his Pike’s Peak creation, a lightweight and all-weather fur felt hat with a high, creased four-inch crown and a wide four-inch brim. Instantly iconic, the hat sold far and wide, equally renowned for its quality and practicality. Working with different shapes and materials, he created hats for city and country, eventually selling millions of hats per year in the half-century that followed, including many styles that we still make today.

Stetson’s entrepreneurial skills were matched by his passion for the well-being of his workers. In an era of meager workers’ rights, Stetson, a devout Baptist, paid good wages and offered extensive benefits to the thousands of people who made a Stetson a Stetson. He provided a robust profit-sharing program, created a building and loan that helped countless workers become homeowners, and built and operated a hospital for employees and the community. He even had an intramural softball league that played during working hours on Wednesday afternoons, among other athletic opportunities. Stetson also helped find the YMCA in Philadelphia and was an early benefactor of Florida’s Deland University, renamed John B. Stetson University in 1889. Its School of Business Administration and College of Law, founded in 1897 and 1900, respectively, were the first of their kind in the state.

Stetson died in Deland in 1906, but his legacy endures. Throughout the 20th Century and on into the 21st, the Stetson has remained an icon of purpose-driven American style, from the dusty ranches of West Texas to the sidewalks of New York. It’s no wonder everyone from the silent film star Tom Mix (who has a hat named after him) to presidents from Truman and LBJ to Ronald Reagan to countless actors, musicians, entrepreneurs, and other modern pioneers have made a Stetson their signature.

They come from all walks of life, but all are bound by a shared appreciation for the quality, character, and a spirit of adventure—and one man’s ingenuity during a fateful Colorado rainstorm more than 150 years ago.

Lon Megaree’s 1922 painting, “The Last Drop from His Stetson,” embodies the cowboy ethos of compassion, integrity, and respect at the heart of every hat we produce today—many featuring a liner adorned with Megaree’s iconic artwork.

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Cowboy State of Mind

Cowboy State of Mind

How a new life on the range in Wyoming—and the loyal companionship of a paint horse named Toby—helped Chance Gilliland get back in the saddle after a debilitating injury.

By Samuel Martin

“Flesh and blood need flesh and blood, and you’re the one I need.” 

— Johnny Cash 

Most cowboys can relate to stories of broken bones. When you’re working with horses, cattle, and large equipment, it’s not a question of if you’ll get hurt but when.

For Chance Gilliland, the fateful moment occurred on a late spring day in 2019 at home in central Missouri. A storm was rolling in, but he just couldn’t fight the urge to ride. “I had gone to the local rodeo the night before and had the itch to be on a horse. When I started to saddle up and mount [my horse], I got thrown and broke my back. I had to be air-evaced to St. Louis, where I had to undergo an emergency spinal fusion.”

The aftermath of his accident was a stark disentanglement from horses and the way of life he knew. Gilliland’s parents, George and Julie, both raced and competed in rodeo and horse shows throughout Chance’s childhood, and he spent his youth riding horses and working with his father. No matter how far he wandered away from home later in life, horses were a constant. Until that day in 2019.

Chance spent the next year and a half in recovery, and for the first time in his life, he experienced anxiety and depression. He spent six months in a brace as he learned how to walk again, and struggled with sleeping and constant pain after returning home from the hospital. He was forbidden to lift anything, so he focused on walkinggoing a little farther each day.

After a year of grueling recovery, it was time for a change. “I grew up watching cowboy movies about the American west and always had this dream of riding my horse through that same open and vast landscape,” recalls Chance, who knew that this was the time to act on that dream. So he pulled up stakes and moved to Wyoming, taking a job as a wrangler on a ranch near the Colorado border, hoping that living and working in the Cowboy State would rekindle his love for riding.

“I’ve never been scared of horses, but after the accident, I was terrified to even be around them. I was fragile. I had lost a lot of confidence, and I didn’t feel like myself,” he says. “As the saying goes, Get back on the horse, but I’ll tell you it’s not easy after an accident like that. You can’t help but consider the possibility of it happening again, and maybe I won’t be as lucky this time.”


“I’ve never been scared of horses, but after the accident, I was terrified to even be around them.”

When Chance arrived at the ranch, he was paired with a large red horse from the wrangler herd. As he tried to throw a blanket on him, he bolted off across the ring. Chance knew this wasn’t the one. A few days later, he heard rumors about a horse named Toby—a hidden gem within the wrangler herd that hadn’t been ridden in a few seasons. 

“The next morning in the dusty air of the stampede, my friend leaned in and said, ‘Thats him,’ and I saw him: white, black, and brown. A galloping paint coming up from the meadow. We met outside the corral and he gave me a nudge.”

Besides their unique coat patterns, paint horses are known for their friendliness, intelligence, and calm demeanor, and Chance’s confidence started to return the moment he climbed onto the saddle. “I saddled him up and went on our first ride and it was just smooth sailing. I felt like myself again, he recalls.

Toby liked to be at the front of the pack and have a strong presence with the other horses, a dynamic that allowed Chance to give Toby the lead while he relearned the lessons of his youth. The two quickly became familiar with one another and spent the summer riding the 30,000 acres across the ranch.

“Toby was there for me when I needed to learn how to ride a horse again,” Chance says. “He helped me lope and trot againall basic stuff, but in a way that was comfortable and safe. A rider and a horse should work together because they’re coworkers, trying to get the job done.

Chance wears the BLACK & TAN JAC-SHIRT.

Chance wears the CLASSIC SUEDE JACKET.

For Chance, the definition of job is an ever expanding one. He recently added “actor” to his résumé following an appearance in the Yellowstone spinoff series 1883, and when not on set, he spends his time at home in Missouri or working on the ranch in Wyoming, riding the open range with Toby.

After an eventful few years, does he have any advice for the rest of us? “Everyone out there can find that horse for you if you look for it, and put the effort into building the relationship.

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The Sky’s the Limit

The Sky’s the Limit

The story of the Stetson Stratoliner

By Paul Underwood

Photography by Steve Gonzalez

The Stetson Stratoliner was made for the man who is going places. Introduced in 1940, it took its name from the Boeing Stratoliner, a milestone in the Golden Age of Aviation. That Stratoliner, designed in 1935, was the first plane with a pressurized cabin, which enabled it to soar up to 20,000 feet—high above troublesome weather systems. This feat of engineering meant the Stratoliner could ferry 33 passengers and six crewmembers further and faster than anyone had flown before. (Among the first to have one? Howard Hughes, whose Stratoliner was dubbed “The Flying Penthouse.”)

Advertisment, 1941

Advertisment in Collier’s, September 1940

Advertisment in Esquire, April 1945

Sensing the implications, the Stetson design team got to work. The result was a lightweight fedora crafted from 2-1/2 ounce fur felt, so it packed easily and could be worn year-round. It sported a lower crown height, the better for fitting into a cramped airplane cabin, or a cab on the way to the airport. Its rakish, angled crown shape suggested a man—or a plane—on the move. The hat band came adorned with a small silver pin in the shape of a Boeing. It even arrived in a metallic silver box, suggesting the famed exterior of its namesake aircraft, with an illustrated label showing both the Stratoliner plane and the Stratoliner name. 

Stetson’s ad campaign for the Stratoliner emphasized the connection between plane and hat. “Take off in style,” one ad urged, while another declared that it “reaches new heights in style, quality and smart colorings”—while “the price is a down-to-earth $6.” Stetson introduced the hat with ads in California and Texas, where some of the first Stratoliner flights touched down. The actor Adolphe Menjou, a noted man of style both on-screen and off, was photographed carrying his Stratoliner hat while boarding a Stratoliner plane, an image soon splashed across Stetson ads far and wide, promising ease, glamour, and sophistication in equal measure. 

“The Stratoliner’s rakish, angled crown shape suggested a man—or a plane—on the move.”

After WWII, as the Jet Age dawned, the hat became the go-to for the era’s Rat Packers and Mad Men. Over time, tastes evolved, and the style was retired, only to return in 2009. Then, as now, it was crafted the old-fashioned way: By hand, in Garland, Texas. While the original Boeing Stratoliner is no longer cutting edge—indeed, the only one left now belongs to the Smithsonian—the hat it inspired remains an icon of timeless Stetson style. 

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Spring 2022: Steve Gonzalez and Ontario Armstrong take the Stratoliner out for a spin in NYC.

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Art & Memories with painter Shane Miller


By Jayme Moye

Photography by Brent Whaley

Nashville-based artist Shane Miller paints landscapes the way they appear in human memory, in fleeting thoughts, or in the recollection of dreams. On his canvas there’s a focal point, but then the opening in the forest, or the bend in the stream, begins to blur and fade. “I feel like that’s how a lot of memories and dreams are,” Miller says. “There’s always one little part that’s in focus, but everything else you can’t really grasp.”

Shane wears the Dune 5X Gun Club Hat in Silverbelly.

“A lot of people will say they bought it because it reminds them of home, or a particular memory.”

Miller, 30, grew up in western Maryland, in the foothills of the Appalachians. His mom homeschooled him for most of his education. He started drawing in early childhood and painting in high school, although playing guitar was his greatest passion. Miller moved to Nashville a couple of years after graduating college, lured by close friends living there and by the music and art scene. He soon got a gig playing guitar for a country music artist, which left his daytime hours open for painting. And once Miller started doing it regularly, he couldn’t stop.

“You know that Picasso quote?” he says, “Art washes from the soul the dust of everyday life.’ It’s really applicable to me. The act of painting, of producing these works, is what keeps me feeling good.”

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While he still enjoys making music, in 2017, Miller officially traded the guitar for the paintbrush as his full-time job. Now, after five years of proving he can earn a living from his landscape painting, Miller’s turning his attention to the pursuit of mastery. “I think it’s important to always try to push yourself to be better,” he says. “I’m hoping to achieve a higher level of discipline with my craft and to keep understanding my painting more and more.”

For Miller, the dream appears to be very much within his grasp.

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Dorset Maple Reserve

Dorset Maple Reserve:

The secret to world-class maple syrup and a better quality of life

By Steve Schwartz

Photography by Maaike Bernstrom

In the Green Mountains of Vermont, the transition from winter to spring means one thing: sugaring season, when the trees are tapped, the sap is boiled, and turned into some of the finest maple syrup in the world.

On a 500-acre piece of land in southern Vermont, Austin Felis II and Lauren Felis are drawing their life and passion from the land, quite literally. As the husband-and-wife owners of Dorset Maple Reserve, they’re producing 5,000 gallons of maple syrup every year, by hand, and operating the entire business by themselves. We headed north to pay their farm a visit and learned the secret to creating a top-quality product while also building a better life for generations to come.

“The quality of working in the woods, taking something from nature, and then refining it into a finished product is pretty rewarding, in my opinion. There’s a lot of self-satisfaction in it. It’s a different world from most and I prefer this one,” Austin said.


Starting in mid-January, he and Lauren clean out 137 miles of tubing around their land to prepare for tapping the trees, where they then strategically drill a 6/10th-inch hole to prevent harming the sugar maple. Then, they put the entire system under a vacuum, which triggers higher production from the tree throughout the tapping process. Then, after reverse osmosis, aeration, and evaporation, they come away with a finished bottle of Dorset Maple Reserve Syrup.

“It’s a different world from most and I prefer this one.”

As Austin explained, the beauty of the syrup doesn’t necessarily come from the process, but moreso from the trees themselves. Much like grapes to wine production, a sugar maple tree is the keystone of a syrup’s flavor, color, and richness. Dorset sits atop a natural marble deposit (it contributed materials for The New York Public Library and many monuments in Washington D.C.), as well as a limestone belt, which gives Dorset syrup a “very soft, almost buttery flavor.” A product from Ohio or Canada may be wildly different from one in Vermont or even neighboring New York.

In other words, every tree and every bottle of syrup is unique, and the same could be said for the people who make it. As for Austin, he opted to return to the farm, which has been in the family for more than 40 years and create the entire syrup operation from scratch. After earning a degree in Management of Technology from Wentworth Institute of Technology in Boston and owning a custom motorcycle shop in Bridgeport, Connecticut, a severe motorcycle crash—along with the birth of his children—prompted Austin and his family to move to Vermont to enjoy a change. “As a younger man, I had zero responsibilities and a lot of freedom. I loved it. As I became a family man and had some real responsibilities when my children came along, my attitude shifted,” Austin said. “I wanted us to live basically a better quality of life.”

Lauren Santagata CHECKS THE GRADE OF THE MAPLE SYRUP PRODUCT. it can only be one of four: Golden, Amber, Dark or Very Dark.

And now a decision for change is the foundation for Austin’s work at Dorset Maple Reserve, something that’s reflected in the product itself. Throughout the course of a season, maple syrup will shift from very light and sweet early on to something much darker and richer and more vibrant in later months. It’s never the same, always taking on more complexity and flavor. This personality and unpredictability is something that Austin and his family have fallen in love with over the years. You could say they’re maple evangelists at this point. One of their most pointed efforts: Giving maple syrup a place beyond the breakfast table. 

“When we first started going direct to the consumer, I noticed that I was having a problem. I would always offer a sample and people would respond, ‘Oh, I don’t eat pancakes.’ My wife and I decided that in order to get to expand people’s ideas, we were going to have to come up with recipes and show people other ways to use it,” Austin said.

If you browse through Dorset’s website, you’ll see recipes for everything ranging from maple-roasted garlic to maple chia pudding and this incredible Cast Iron Bourbon Apple Crisp. They’ve even introduced a bourbon barrel-aged syrup and smoked and spicy syrup, which make up more than half of their total sales. Austin and Lauren see maple syrup as much more than an alternative to sugar, though. As something that’s loaded with zinc, magnesium, and riboflavin, maple syrup is a vegan-approved way to boost your immune system, much like honey. There are even some studies that link maple syrup with a reduction of heart disease and certain cancers, Austin said, and it all comes from a 6/10th-inch hole drilled into a tree. 


It seems that the world at large is beginning to take notice, too, as Dorset has seen steady growth since opening its doors in 2013. Call it a farm-to-table movement or just people recognizing a great product when they see one, but a change for the better seems to follow Austin and Lauren. Now, with their three children getting older, Austin said he hopes this 500-acre maple syrup farm will be something he can share with generations to come. 

“I want to build a future for my kids. This farm is one of the most beautiful pieces of property I’ve ever seen. I want my children and my grandchildren and my great-grandchildren—I want everybody—to enjoy it,” Austin said.

Until then, they’ll keep drawing inspiration from the land. As of March, Austin and Lauren were hard at work, preparing their maple syrup for their growing customer base. Each bottle represents something new and unique, a flavor growing more rich and complex with each passing week, much like the lives of the people who are producing it. And soon, after hours of hands-on production and attention, people around the world will get a taste of this positive change for themselves, one bottle at a time. 

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The Open Road Story


Widely imitated, never replicated, since 1937

By Paul Underwood

Every now and again, form and function intersect to create something somehow both useful and beautiful, purpose-built yet iconic. The Coca-Cola bottle. The denim work shirt. The Porsche 911. To that list we would add: The Stetson Open Road, a style so classic and time-tested that it’s hard to believe there was ever a world where it didn’t exist.

The hat, with its western crown and shorter, town-friendly brim, dates back to 1937, a time when the open road itself was a relatively new concept. Route 66 was just over a decade old, and the top-of-the-line V-8 in the latest-model Ford cranked out a whopping 85 horsepower. Unlike today’s sturdy, hard-wearing Open Road, the 1937 iteration was more of a lightweight, western-inflected fedora.

It wasn’t until 1948 that the Open Road as we know it—with its iconic cattleman crown, narrow grosgrain ribbon, and that perfectly proportioned brim turned up just so at the edge—entered the world. It was an instant success, thanks in part to a marketing campaign that blanketed Texas and other Western states, proclaiming the hat’s versatility as a dressy option at home in town or country, in the West or back East. (“Almost as popular on the Avenue as they are on the Open Road,” as one ad later put it.)

Advertisment in The Saturday Evening Post, 1950

Advertisment, 1952

Advertisment in Time, February 1953

Before long, the Open Road was adorning some of the most famous heads in the land. Presidents in particular seemed to relish the style—Harry S. Truman was an early adopter, as was Dwight Eisenhower, both of whom wore it with a suit. 


Lyndon B. Johnson’s affinity for the Open Road inspired both a Stetson ad campaign (touting “The L.B.J. Look”) and a wave of knockoffs in the mid-’60s. (You can still buy your own—authentic—Open Road at the LBJ Ranch near Johnson City, Texas.) Winston Churchill wore one; so did Hank Williams. The hat played a supporting role in films like Smokey and the Bandit and From Dusk Till Dawn, while modern luminaries including Jeff Tweedy of Wilco have helped ensure the hat’s legend endures in the 21st Century.

Before long, the Open Road was adorning some of the most famous heads in the land.

In the early days, Stetson ads declared the Open Road “a hat that will proclaim your distinctive individuality to the world”—a sentiment that rings more true now than ever. You can get an Open Road in straw, hemp, or, of course, fur felt, each one adorned with our new 1865 pin. As it has been for decades, the Open Road is made by hand in Garland, Texas, meaning only a handful are in production at any one time.

Quality takes time, as we like to say, but, as the Open Road proves, quality also endures.

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