Some cowboy hats are as iconic as the movies they’re in
Western movies have been a staple of cinema since they first appeared in the late 1800s. Audiences love following stories of good guys fighting bad guys, outlaws robbing banks, and sheriffs chasing robbers on horseback. Cowboys always seem so cool with their sense of swagger, and their fashion choices usually complement their attitudes. Their sense of style often precedes their reputation, and great cowboy hats can be as iconic as the movies they appear in.
When you think of Western movie stars, several names immediately come to mind: John Wayne, Gary Cooper, Jimmy Stewart, and Clint Eastwood, to name a few. Modern-day cowboys like Jeff Bridges, Russell Crowe, and Benedict Cumberbatch have carried on the Western tradition and have added their personal touch to the genre. All of these actors have worn quintessential cowboy hats in films over the last ten decades, and these are some of the best cowboy hats in movies.
10, John Wayne in The Shootist
John Wayne is the most iconic Western actor that ever lived. Born in Iowa in 1907, Wayne appeared in countless rewatchable movies, mostly throughout the 1950s and 1960s. Some of his most iconic movies include Red River (1948), True Grit (1969), and The Cowboys (1972). One of his most iconic movie looks, however, came near the end of his career in 1976.
The Shootist is a Western movie directed by Don Siegel based on the book of the same name by Glendon Swarthout. Wayne plays J.B. Books, an aging gunslinger who rents a room from a widower (Lauren Bacall) in Nevada. Several shady criminals come to visit Books, so he sets up a trap at a saloon to ambush them. In The Shootist, Wayne wears his favorite cowboy hat – a grey silver belly hat with a diamond-crested crown. It also ended up being his last.
9, Paul Newman in Butch Cassidy and the Sundance Kid
In 1969’s Butch Cassidy and the Sundance Kid, Paul Newman plays Butch Cassidy, while Robert Redford plays the “Sundance Kid”. The pair are on the run after a string of train robberies, being chased by the United States posse the whole way. They escape to Bolivia, but find the culture shock to be too much to create a sustainable life.
Newman is famous for many roles, many that we can’t live without. His look in Butch Cassidy and the Sundance Kid is classic for Hollywood fashion of the 1960s. He wears a tan work jacket with a rabbit fur felt hat. Newman went on to star in a lot of different movies until his tragic passing in 2008, but his look in Butch Cassidy is the most iconic.
8, Lee Van Cleef in For a Few Dollars More
Lee Van Cleef was the ultimate Western tough guy in both movies and real life. He was a World War II veteran who was awarded a Bronze Star for his work as a minesweeper. He often starred in Italian Spaghetti westerns, including Sergio Leon’s 1965 Dollars Trilogy film For a Few Dollars More. In the movie, Van Cleef plays Colonel Douglas Mortimer, a bounty hunter who teams up with Manco (Cl int Eastwood) to capture a dangerous prisoner named “El Indio” (Gian Maria Volonte).
Van Cleef wears a black, wide-brim cowboy hat in For a Few Dollars More. It’s an Argentine-style hat with a 3″ crown, and it’s made of suede fur felt. The actor returned and sported the same hat for Leone’s Dollars Trilogy follow-up The Good, the Bad, and the Ugly in 1966, only he played a different character. In that film, Van Cleef, played Angel Eyes (“the bad”), a ruthless killer who takes pleasure in always finishing the job.
7, Clint Eastwood – The Good, the Bad, and the Ugly
Speaking of The Good, the Bad, and the Ugly, it would be a crime to not mention Eastwood’s character and look in the film. He plays Mancho (“The Man with No Name”), an outlaw who teams up with a wanted bandit named Tuco to scam desert towns out of money. Mancho often turns Tuco in for the reward money offered for his capture, only to shoot him down from a rope at the last minute when he is inevitably sentenced to be hanged.
Mancho’s hat in the film is iconic, but it’s a bit of a mystery as to what type of cowboy hat it is. It’s believed Eastwood purchased the hat himself in Los Angeles, then brought it to Spain for shooting on location. Keen-eyed fans have noticed that the hat’s buckle seems to switch sides a couple of times in the film, but could be because the band seems to be reversible.
6, Sam Elliott – The Big Lebowski
Sam Elliott has the look and voice of a real cowboy. One of his first roles was as a card player in the aforementioned Butch Cassidy and the Sundance Kid. He was born in Northern California and moved to Los Angeles in the 1960s to be an actor. Since then, he’s gone on to star in several iconic movies, both westerns, and non-westerns, including 1989’s Road House, 1993’s Tombstone, and 1998’s The Big Lebowski.
In the latter, Elliott plays “The Stranger”, a man who acts as the narrator for the movie but appears at the end. It’s hard to tell whether Elliott wears a standard Stetson hat or a Gus-style hat in his limited screen time, but either way, it’s a classic look. The Stranger reveals to Jeffrey “The Dude” Lebowski that he’s going to be a father, as his wife Maude (Julianne Moore) is pregnant. The Big Lebowski may have flopped at the box office, but it’s become a cult classic since its release.
5, Hailee Steinfeld – True Grit
Hailee Steinfeld is one of the best female actors out there today. She starred as Kate Bishop in the Disney+ series Hawkeye and recently voiced Gwen Stacy/Spider-Woman in 2023’s Spider-Man: Across the Spider-Verse. But several years before that, she got her big break starring alongside Jeff Bridges in the Coen brother’s 2010 Western remake True Grit.
In the movie, Steinfeld plays a determined 14-year-old girl named Mattie Ross who hires a lawman named “Rooster” Cogburn to avenge her father’s death. The problem is, Rooster is an alcoholic who is barely able to shoot straight at the best of times. Steinfeld’s hat in the film was made by Baron, a manufacturer that specializes in making movie and TV hats.
4, Jeff Bridges – True Grit
Rooster’s (Bridges) hat in True Grit is also very iconic. Instead of going for a classic cowboy hat, the Coen brothers chose a unique hat to match the character’s gritty look. It’s a standard hat from the American Costume Company, but it has some interesting characteristics. It has a pinched peak and features bullet holes and moth holes crafted by the costume department specifically for the movie.
Apparently, there were copies of Bridges’ iconic hat on set, but the actor ended up wearing the same hat for the duration of shooting. Maybe the look helped True Grit become one of Jeff Bridges’ best dramas. It’s hard to know how much Bridges’ actual hat from the movie is worth in 2023, but it sold for more than $12,000 at an auction back in 2013.
3, Val Kilmer – Tombstone
In 1993’s Tombstone, Val Kilmer plays Doc Holliday. When Wyatt Earp (Kurt Russell) tries to leave his gunslinging ways behind him, he doesn’t get far. Earp wants to settle down in Tombstone, AZ to start a business with his brothers, but he just can’t escape his past. Instead, he enlists his buddy Holliday to help the troop fight against the oncoming Cowboy gang.
Kilmer’s hat in the movie was custom-made by Tom Hirt, who was the official hatmaker for the film. It’s made of high-quality beaver-felt and features a silk lining for superior comfort. It also features a hand-curled brim, which Hirt claims “cannot be duplicated.” You can still buy a replica of the hat from Val Kilmer’s online store, for the cool price of $895 plus tax.
2, Russell Crowe – 3:10 to Yuma
James Mangold’s 2007 film 3:10 to Yuma is a remake of the 1957 film of the same name. It stars Russell Crowe as a captured outlaw named Ben Wade. A disabled rancher named Dan Evans (Christian Bale) who is desperate for cash is hired to lead a posse that will take Wade to Contention, where he is to board an afternoon train at 3:10 pm to Yuma Territorial Prison. Wade, of course, has other plans.
Russell’s character in the movie is ruthless and rugged, and his outfit matches his personality. His cowboy hat has a low telescope crown and a small brim. It was chosen to match the period of the film as it was a very popular style from the 1860s to 1880s. It must have worked for Crowe, too, as 3:10 to Yuma is easily one of James Mangold’s best films.
1, Benedict Cumberbatch – The Power of the Dog
The most recent best cowboy hat in film history is Benedict Cumberbatch’s hat in Jane Campion’s 2021 Western drama The Power of the Dog. Cumberbatch plays Phil Burbank, a tough rancher who is mean to others but secretly hides part of his identity. With powerful performances, tense dialogue, and beautiful cinematography, The Power of the Dog is one of the best movies on Netflix.
Cumberbatch’s cowboy hat in the movie was chosen to match the Western aesthetic of the 1920s, which is when the movie takes place. Some of the pieces of the wardrobes in the film were purchased at Western Costume, a shop founded in California in 1912 to serve the movie industry. The Power of the Dog was nominated for 11 Academy Awards, including Best Picture and Best Director.