The Original Cliff Booth Watch Worn by Brad Pitt Returns for 2026
ON STAGE • FILM & TELEVISION
Brad Pitt’s Academy Award-winning portrayal of Cliff Booth helped transform a vintage-inspired timepiece into one of modern cinema’s most recognizable style statements.
The Original Cliff Booth Watch Worn by Brad Pitt Returns for 2026
Created by the Los Angeles studio behind the original watch band worn by Brad Pitt in Once Upon a Time… in Hollywood, the Cliff Booth Legend 2026 Edition reimagines a cinematic icon for modern collectors.
Tobacco / Gold
Warm tobacco leather paired with gold-tone hardware for a vintage-inspired look that feels sun-worn, cinematic, and unmistakably classic.
Black / Silver
Deep black leather paired with silver-tone hardware for a cleaner, more understated interpretation of the Cliff Booth Legend.
Shop the Cliff Booth Legend 2026
From Screen Legend to Modern Classic
There are movie characters.
And then there are legends.
When Quentin Tarantino’s Once Upon a Time… in Hollywood introduced audiences to Cliff Booth, portrayed by Brad Pitt, the character immediately became a style icon. Effortlessly cool, understated, rugged, and timeless, Cliff Booth embodied a distinctly American attitude that still resonates years later.
In 2020, Brad Pitt earned the Academy Award for Best Supporting Actor for his portrayal of Cliff Booth, cementing the character’s place in modern film history.
For Red Monkey Designs, the connection runs deeper than inspiration. Red Monkey created the custom leather watch band worn by Brad Pitt as Cliff Booth in the film.
That original piece became part of the character’s unmistakable look.
Years later, collectors, film enthusiasts, and watch aficionados still search for the timepiece that helped define Cliff Booth’s style. The enduring popularity of both the character and the vintage Bullhead aesthetic led Red Monkey to revisit the concept for a new generation.
Built From a Piece of Film History
The timepiece that helped define Cliff Booth’s on-screen style was inspired by the beloved vintage Citizen Bullhead — a watch known for its distinctive case shape, racing-era attitude, and unmistakable 1970s character.
The Cliff Booth Legend 2026 Edition is not a replica.
It is an evolution.
Inspired by the spirit of the original watch and built upon Red Monkey’s connection to the film, the 2026 Edition reimagines the look for modern collectors, everyday wear, and a new era of Red Monkey design.
Modern proportions. Updated styling. Classic attitude.
Brad Pitt, Red Monkey, and On-Screen Style
Red Monkey’s connection to Brad Pitt extends beyond Once Upon a Time… in Hollywood. Pitt has also worn Red Monkey watches in The Mexican and Ocean’s 13, including his own personal Red Monkey watch in Ocean’s 13.
Those appearances are part of Red Monkey’s larger history of building leather pieces for artists, actors, stylists, musicians, and production teams across stage, television, and film.
Not a Replica. An Evolution.
The Cliff Booth Legend 2026 Edition was never intended to recreate the past exactly.
Instead, Red Monkey set out to capture what made the original so compelling: the rugged California attitude, the vintage racing influence, the quiet confidence, and the lived-in character that made Cliff Booth’s style feel authentic.
The result is a modern Red Monkey timepiece born from one of cinema’s most recognizable style moments.
Built for today.
Born from a piece of film history.
Designed in Los Angeles
For more than 30 years, Red Monkey Designs has created custom leather pieces for musicians, actors, artists, stylists, and production teams.
From stage to screen, Red Monkey has built pieces worn by some of the most recognizable names in music and entertainment.
The Cliff Booth Legend 2026 Edition continues that story — taking a piece of Red Monkey film history and evolving it into a modern timepiece for collectors, film fans, and anyone drawn to timeless American style.
Available Now
The Cliff Booth Legend 2026 Edition is available now in Tobacco / Gold and Black / Silver.
Designed in Los Angeles.
Built by Red Monkey.
Worn on screen.
Built to become a legend.
Shop the Cliff Booth Legend 2026
Frequently Asked Questions
Who made the watch band worn by Brad Pitt as Cliff Booth?
Red Monkey Designs created the custom leather watch band worn by Brad Pitt as Cliff Booth in Once Upon a Time… in Hollywood.
Explore the Cliff Booth Legend 2026 Collection .
Is the Cliff Booth Legend 2026 Edition a replica?
No. The Cliff Booth Legend 2026 Edition is a modern interpretation inspired by the vintage Bullhead aesthetic and Red Monkey’s connection to the original film.
Did Brad Pitt wear Red Monkey watches in other films?
Yes. Brad Pitt has also worn Red Monkey watches in The Mexican and Ocean’s 13, including his own personal Red Monkey watch in Ocean’s 13.
What colors are available?
The Cliff Booth Legend 2026 Edition is available in Tobacco / Gold and Black / Silver.
Where can I see more Red Monkey On Stage stories?
Explore more artist, stage, film, and television stories in the Red Monkey On Stage archive .