Steffi BakerIn the Old West — and in the movies — a cowboy was never without his hat. It kept his eyes, face and scalp protected from the blistering sun.

Picture John Wayne or Clint Eastwood riding the range…

In today’s world, a cowboy hat could also be a rare, coveted investment piece worth a pretty penny.

And the most prized brand is the Stetson.

Besides being arguably one of the most iconic American brands, the Stetson also represents the classic American tale of getting rich — by starting a business.

How a Hat Company Was Born

John Batterson Stetson was no cowboy in the beginning… Born and raised in New Jersey, he came from a long line of renowned hat-makers. Then, during his teen years working for his father, he contracted tuberculosis. In 1860, Stetson headed to Colorado to recover.

It was there Stetson turned his mind to mining. He intended to become a gold miner — but it didn’t quite pan out that way…

Using what he had learned in the family business, Stetson began making waterproof blankets, and then turned his hand back to hats.

His design — with a high crown and a broad brim — offered favorable protection from the elements. After he sold one for $5, he decided to launch a business: The John B. Stetson Co.

Go West, young man: John B. Stetson…

(Source: FindAGrave)

Stetson went back east, borrowed $60 from his sister and set up shop in Philadelphia. In a clever marketing move, he sent samples of his first model — named “Boss of the Plains” — to hat dealers in Western states, requesting orders.

The hats caught on immediately as there was a void in the market for men’s headwear at the time. Decorative pieces like the top hat and the derby that were popular in the east weren’t practical for daily life out West.

John B. Stetson died in 1906, but his heirs kept the company going strong. Shortly after the turn of the century, Stetson was the biggest hat company in the world, with over 5,000 employees constructing more than 3 million hats per year.

Movie stars and celebrities started wearing Stetsons, as they came to be known (easier than saying “Boss of the Plains”). But the biggest Stetson promoters turned out to be famous frontier folk like William “Buffalo Bill” Cody, Calamity Jane and Annie Oakley, who were rarely photographed without their famous hats on.

Annie Oakley Stetsons hat

Annie Oakley’s Stetson sold at auction in Dallas in 2012 for over $17,000…

(Source: Heritage Auctions)

In a pinch, the Stetson could serve as far more than just a hat… The Texas State Historical Association says the “Texas Rangers adopted the hat and found that it could be used to drink from, to fan a campfire, to blindfold a stubborn horse, to slap a steer, to smother grass fires and to serve as a target in gunfights. It could also be brushed for dress wear.”

Now, that’s one heck of a hat.

Its versatility along with its style are the two main reasons people were (and still are) happy to pay a premium to own a Stetson. From that first $5 sale to the present — when basic models start at over $100 — the quality John B. Stetson built in to his product created many loyal customers.

From Dud to Dandy Once Again

After introducing a women’s line in the 1930s, sales peaked in the 1940s. The late ’50s ushered in a decline in the company’s fortunes when the practice of wearing hats on a daily basis went out of fashion.

The ’60s were a disastrous era for the once-mighty company and a nonfamily majority shareholder was able to seize control of the company. He shut down the manufacturing operation and the company was reduced to simply licensing the name. It barely survived the ’70s.

In the 1980s, the cowboy hat came roaring back into style thanks to the films Urban Cowboy (1980) and the Indiana Jones series, which started in 1981.

The resurgence in popularity has lasted. Now avid collectors have created such a demand that these hats can sell for thousands on the secondary market.

Urban Cowboy

The movie Urban Cowboy features John Travolta, Debra Winger, a mechanical bull and lots of Stetsons…

Current models as well as vintage hats are sought after. They can run from $500–5,000. A number are listed on eBay. In Western and Southwestern states, particularly Texas, you’re likely to find them being traded at rodeos and other cowboy-related events.

The “most wanted” models change, but a quick internet search can tell what what’s currently in demand. If you can buy one under auction price, you can make yourself a quick return on an American classic.

Believe it or not, there’s also a global market for Stetsons. You may find that a hat will fetch even more in Europe or Asia than stateside.

Urban Cowboy

Here’s an eBay listing for a vintage hat owned by a Japanese collector…

So if you grew up watching great American Westerns by John Wayne and John Ford… if you possess a frontier spirit of your own… or if you simply have a penchant for classic headwear… you may want to look into investing in a Stetson.

Pioneer profits from off the beaten path… who knew?

To your wealth,

Steffi Baker

Steffi Baker
Editor-at-large, Unconventional Wealth

P.S. As an asset, Stetsons are pretty niche. Certainly, their place in the history books adds to their value… I want to know if you’ve invested in any historical artifacts — anything that relates to our history as a nation. Bonus points if it’s got a good story. Send me an email (and perhaps a photo) to

Steffi Baker

Steffi Baker is the editor-at-large of Unconventional Wealth. For the past 10 years, she worked with a small strategy consulting firm that dealt exclusively with wealth-management companies, helping them market themselves to ultra-high-net-worth clients.

Through this line of work, Steffi attended events in London and New York and hobnobbed with household names and international...

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