Evolution of Cowboy Hats in Pop Culture and Film

The cowboy hat has become much more than a tool of the American frontier. From the cattle ranches of the Old West to modern-day music festivals and red carpets, it has evolved into a symbol of rugged independence, rebellion, and style. Throughout history, film, television, and popular culture have played crucial roles in shaping the perception of cowboy hats, turning them from functional headgear into cultural icons.

For those new to owning a cowboy hat, you’re not just purchasing a piece of fashion—you’re stepping into a world rich with tradition, pop culture history, and enduring influence. In this article, Heartland Hatters explores the evolution of cowboy hats in film and pop culture, and offers tips on caring for your hat so you can enjoy it for years to come.

Before cowboy hats hit the silver screen or Instagram, they were an essential part of life on the frontier. In the 19th century, hats varied widely—some cowboys wore bowler hats, sombreros, or coonskin caps. But it was John B. Stetson’s invention of the “Boss of the Plains” hat in 1865 that solidified what we now recognize as the cowboy hat. Stetson designed the hat to provide shade, protection from rain, and durability for rugged outdoor conditions, and its simple design became a staple for ranch hands and cattlemen.

The Stetson brand, synonymous with cowboy hats, would go on to feature prominently in the world of cinema, setting the stage for the cowboy hat to become more than just a piece of practical gear—it became a symbol of an idealized American spirit.

The evolution of the cowboy hat’s iconic status began in the early days of cinema, with silent Westerns in the 1910s and 1920s establishing the cowboy as the quintessential American hero. Films featuring stars like William S. Hart and Tom Mix set the stage, but it was the advent of sound that cemented the cowboy hat as a symbol of honor, adventure, and rugged masculinity.

John Wayne: The Cowboy Hat’s First Hollywood Superstar

The 1930s through the 1950s saw the rise of Westerns in Hollywood, and no star was bigger than John Wayne. Known for his towering frame, square jaw, and iconic gait, Wayne’s characters often wore wide-brimmed hats, cementing the association between the cowboy hat and the stoic, honorable American man. Films like Stagecoach (1939) and True Grit (1969) made his Stetson hat just as recognizable as his on-screen persona.

Wayne’s signature hat style—a low, creased crown with a wide brim—became a Hollywood standard for decades to come. The cowboy hat wasn’t just a practical accessory; it was part of the myth-making machinery that shaped American ideas about the West.

Roy Rogers and the Glamour of the Cowboy Hat

While John Wayne's characters often embodied grit and stoicism, Roy Rogers introduced a more glamorous, almost show-business side to the cowboy hat. Rogers’ hats, often adorned with decorative bands or silver embellishments, were part of a larger, glitzier aesthetic that tied country music and cowboy culture together. His white, crisply brimmed hats reflected a cleaner, idealized vision of the American cowboy.

As Western films evolved in the 1960s, they began to reflect the growing complexities of society, and with them came a shift in the portrayal of the cowboy. Clint Eastwood, particularly in his work with Italian director Sergio Leone, became the face of this change. His roles in the "Spaghetti Western" genre revolutionized the archetype of the cowboy, moving away from the clean-cut, morally infallible heroes of previous decades toward a more morally ambiguous, cynical anti-hero.

Clint Eastwood’s Impact on the Cowboy Archetype

In films like A Fistful of Dollars (1964), For a Few Dollars More (1965), and The Good, the Bad and the Ugly (1966)—collectively known as Leone’s "Dollars Trilogy"—Eastwood portrayed "The Man with No Name," a character who embodied rugged individualism and operated by his own moral code. This character was often taciturn, unsentimental, and opportunistic, willing to work both sides of the law to achieve his ends. The cowboy in these films was no longer a shining example of justice and righteousness, but rather a survivor in a harsh world, shaped by the morally grey terrain of the post-Civil War West.

The shift in the cowboy hat’s aesthetic mirrored this character transformation. Eastwood’s hats were gritty, sweat-stained, and often pulled low over his eyes, reflecting the harshness of the environment and the internal struggle of his characters. His hats were far removed from the pristine styles worn by earlier Western heroes like John Wayne. The wide-brimmed, beaten-up hats worn by Eastwood symbolized a world where survival and self-preservation were paramount, and this added to the growing allure of the cowboy as an anti-hero.

In Eastwood’s films, the cowboy hat became a symbol of both protection and isolation. His characters were loners, drifting from town to town, their hats shielding them not just from the elements but from emotional vulnerability and connection. Unlike earlier cowboy hats, which might have been spotless or well-maintained, Eastwood’s hats were part of the character’s identity—weathered and battered, showing the wear and tear of a life on the edge. This visual change was subtle but crucial. In many ways, the condition of the hat told you everything you needed to know about the character wearing it.

For example, in The Good, the Bad and the Ugly, Eastwood’s iconic brown, tattered hat not only enhanced his rugged image but also differentiated him from his co-stars. Lee Van Cleef’s character, "Angel Eyes," wore a darker, sharper, more villainous hat, while Eli Wallach’s "Tuco" sported a somewhat disheveled hat, reflecting his chaotic, wild nature. These subtle choices in hat styles underscored each character’s role in the film, creating a visual shorthand for their moral alignments and intentions. This helped cement the notion that the cowboy hat was not just a piece of functional gear but an integral part of character development in Westerns.

The Spaghetti Westerns, which were low-budget Italian films shot with a distinctly European flair, introduced a gritty realism that hadn’t been seen in American Westerns before. Eastwood’s hat, along with the dust, sweat, and grime that covered his character, reflected this more grounded approach. Unlike Hollywood’s polished Westerns, Spaghetti Westerns showcased a dirty, harsh version of the frontier, where lawlessness reigned, and survival often required ruthless pragmatism.

The cowboy hats worn by Eastwood in these films, typically made from felt, were practical but intentionally unpolished. The once-vibrant colors were faded from long hours in the sun, and the brims were crumpled from years of rough handling. This visual storytelling allowed audiences to immediately understand that these characters had been through countless hardships, that their lives were shaped by danger and scarcity. The very condition of the cowboy hat became a narrative device—something that told you as much about the character as their actions or words.

Moreover, this portrayal marked a clear departure from the virtuous, upright lawmen of earlier Westerns. The evolution of the cowboy hat into something so worn and weathered was reflective of a larger cultural shift. By the 1960s, American audiences were questioning institutions of power and traditional narratives of heroism, and the Spaghetti Western, with its morally ambiguous anti-heroes, resonated with the countercultural movements of the time.

Clint Eastwood’s portrayal of the cowboy anti-hero and his gritty, weathered hats continued to influence Westerns well into the 1970s and beyond. In films like High Plains Drifter (1973) and The Outlaw Josey Wales (1976), Eastwood built on his earlier work, portraying characters who were haunted by their pasts, cynical about the future, and distrustful of authority. The hats in these films followed the same pattern—rough, lived-in, and deeply personal to the character wearing them.

In The Outlaw Josey Wales, Eastwood’s character is a Confederate soldier turned outlaw, and his wide-brimmed hat reflects his journey from soldier to fugitive. The hat, much like the character himself, is caught between worlds—representing the harsh reality of survival in post-Civil War America, where law and order were elusive, and vengeance often drove men to the edge of morality.

Clint Eastwood’s influence extended beyond Westerns and into broader pop culture, shaping how cowboy hats were perceived in other genres. As the anti-hero became a more prominent figure in film and television, the battered, low-brimmed cowboy hat became a symbol of rebellion and individualism. The cowboy hat, once worn by white-hatted heroes who symbolized law and justice, now represented complex figures who operated outside traditional moral codes.

Eastwood’s style even influenced later Westerns like Quentin Tarantino’s Django Unchained (2012), where the titular character, played by Jamie Foxx, adopts a cowboy hat as part of his transformative journey from slave to bounty hunter. Similarly, the Red Dead Redemption video game series, which draws heavily from Eastwood’s films, features a protagonist who dons a wide-brimmed, weathered cowboy hat—signifying his struggle for survival and redemption in the unforgiving landscape of the American West.

Even though the classic Western genre has waned in popularity, the cowboy hat has continued to evolve, making appearances in various aspects of pop culture, music, fashion, and even social media. Today, cowboy hats are as much a part of modern celebrity culture as they are of film, with many stars incorporating them into their everyday looks or stage personas.

Few subcultures have kept the cowboy hat alive quite like country music. Artists like Johnny Cash, Dolly Parton, and Willie Nelson have sported cowboy hats for decades, reinforcing the deep ties between country music and Western fashion. But modern country stars have taken it to a whole new level.

Garth Brooks became synonymous with the black cowboy hat in the 1990s, often pairing his hats with flannel shirts and cowboy boots, a look that has since become a staple for country music fans. Today, artists like Luke Bryan, Kacey Musgraves, and Miranda Lambert keep the cowboy hat alive at concerts and festivals, turning it into a must-have accessory for anyone attending events like Stagecoach or CMA Fest.

Even non-country artists have adopted the cowboy hat in their styles. Beyoncé rocked a stunning black cowboy hat in her Formation video and during her "Renaissance World Tour," blending Western influences with high fashion. Similarly, Lil Nas X mixed traditional Western wear with modern street style in his Old Town Road music video, catapulting the cowboy hat back into the mainstream.

Red Carpet and Fashion Week: The Cowboy Hat’s High Fashion Moment

The cowboy hat has not only stayed relevant in music—it has also been embraced by the fashion industry. High-end designers have incorporated cowboy hats into their collections, bringing this traditionally rustic item onto runways and red carpets.

Luxury brands like Dior, Gucci, and Ralph Lauren have featured cowboy hats in their fashion lines, pairing them with couture outfits in a way that fuses Western heritage with contemporary trends. Celebrities like Timothée Chalamet and Billy Porter have also sported cowboy hats on the red carpet, showing how versatile this once utilitarian headpiece has become.

The Met Gala—fashion’s biggest night—has also seen its fair share of cowboy hats. During the 2021 “In America: A Lexicon of Fashion” Met Gala, stars like Lil Nas X and Jennifer Lopez embraced Western-inspired outfits, accessorizing with cowboy hats and reinterpreting them in a high-fashion context.

TV Shows and the Rebirth of Western Culture

The recent popularity of shows like Yellowstone (2018-present) and 1883 has brought cowboy hats back into the limelight. The characters in these series, particularly those played by Kevin Costner and Taylor Sheridan, wear cowboy hats as part of their everyday lives, bringing back the rugged, stoic cowboy image from classic Westerns, but with a modern twist.

Costner’s character, John Dutton, has sparked a resurgence in interest in traditional rancher-style cowboy hats. Modern viewers, even those far removed from life on the range, find themselves drawn to the romanticized yet gritty portrayal of ranch life. This renewed interest in cowboy hats as part of mainstream fashion reflects a broader trend toward Western-style clothing that blends heritage with contemporary style.

The Cowboy Hat in Social Media and Fashion Influencers

In recent years, cowboy hats have become trendy in unexpected places. Coachella, the California music festival known for its bohemian vibes, has become a hotbed for cowboy hats. Influencers and celebrities alike have embraced the hat as a staple of festival wear, pairing it with everything from fringe jackets to flowy dresses.

On platforms like Instagram and TikTok, influencers like Addison Rae, Bretman Rock, and Kylie Jenner have all been spotted donning cowboy hats, bringing Western wear into the world of Gen Z fashion. Whether it’s a traditional Stetson or a brightly colored felt hat, the cowboy hat’s versatility and timeless appeal have made it a favorite among younger audiences, many of whom are discovering the charm of Western wear for the first time.

For those just beginning their cowboy hat journey, picking the right hat might feel daunting. With the rich history and deep pop culture connections we’ve covered, your hat can symbolize much more than function. Here’s what to consider:

• Material: Cowboy hats come in two primary materials—felt and straw. Felt hats, often made from wool or fur, are best for colder climates and formal settings. Straw hats are lightweight and breathable, perfect for summer or outdoor events.
• Crown and Brim Style: Whether you prefer the high, creased crown of a cattleman hat or the rounded look of a gambler, the style you choose can reflect different elements of cowboy culture or modern trends. Likewise, brim sizes vary from wide and practical to smaller and more fashion-forward.
• Color: While classic black and brown remain popular, today’s cowboy hats come in every shade imaginable. Stars like Kacey Musgraves have popularized pink and pastel cowboy hats, offering a fresh, modern twist on traditional headgear.

The Legacy and Future of the Cowboy Hat

From Hollywood’s early Westerns to today’s music festivals and runways, cowboy hats have proven their staying power. They remain symbols of rugged independence, American heritage, and rebellion. Whether you’re wearing your cowboy hat as a fashion statement or as a nod to tradition, you’re participating in a legacy that spans more than a century of pop culture.

At Heartland Hatters, we’re proud to continue this legacy by offering high-quality cowboy hats for every occasion. As cowboy hats remain a fixture in both everyday life and modern media, there’s no better time to embrace this timeless style.