Cliff Booth Legend 2026 | The Original Watch Worn by Brad Pitt
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Red Monkey Designs • Watches
The Original Cliff Booth Watch Worn by Brad Pitt
The Red Monkey leather watch cuff worn by Brad Pitt as Cliff Booth in Quentin Tarantino’s Once Upon a Time in Hollywood — reintroduced for the Cliff Booth Legend 2026 Collection.
Some accessories are fashionable.
Others become legendary.
The Cliff Booth Legend 2026 Collection celebrates one of the most recognizable leather watch cuffs ever worn on screen: the original Red Monkey watch band worn by Brad Pitt as Cliff Booth in Quentin Tarantino’s Once Upon a Time in Hollywood.
What began as a custom-built leather watch cuff for a major motion picture quickly became one of the most requested pieces in Red Monkey history.
Hand-built in Los Angeles using premium heavy-weight leather and stainless steel hardware, each Cliff Booth watch captures the rugged spirit, vintage attitude, and effortless cool that made the character an instant modern icon.
Built for everyday wear and designed to age beautifully over time, the Cliff Booth Legend Collection combines vintage military inspiration, classic Americana styling, and Red Monkey’s signature leather craftsmanship.
Why the Cliff Booth Watch Became Legendary
- Worn by Brad Pitt as Cliff Booth in Once Upon a Time in Hollywood
- Original Red Monkey leather watch cuff design
- Hand-built in Los Angeles
- Premium heavy-weight leather construction
- Stainless steel hardware
- Vintage-inspired military styling
- Designed to develop character and patina over time
- Built in limited 2026 availability
More Than a Watch
The Cliff Booth watch is more than a timepiece.
It is a piece of modern film history, built with the same Los Angeles craftsmanship that has defined Red Monkey Designs for more than three decades.
Each watch in the Cliff Booth Legend 2026 Collection is hand-built to order using premium leather selected for feel, structure, durability, and long-term character.
Whether you know it as the Cliff Booth watch, the Brad Pitt watch from Once Upon a Time in Hollywood, or the original Red Monkey leather cuff watch, this collection carries a story that goes far beyond the wrist.
Built in Los Angeles Since 1995
Red Monkey Designs has been hand-building premium leather goods in Los Angeles since 1995, creating guitar straps, belts, cuffs, watches, and stage-worn pieces for musicians, artists, collectors, and film productions around the world.
The Cliff Booth Legend 2026 Collection continues that legacy with a watch cuff that feels rugged, timeless, collectible, and unmistakably Red Monkey.
Frequently Asked Questions
Was the Cliff Booth watch really worn in Once Upon a Time in Hollywood?
Yes. The original Red Monkey leather watch cuff was worn by Brad Pitt as Cliff Booth in Quentin Tarantino’s Once Upon a Time in Hollywood.
Is this the same Cliff Booth watch design worn by Brad Pitt?
The Cliff Booth Legend 2026 Collection is built from the original Red Monkey design worn by Brad Pitt as Cliff Booth in the film
Where are Red Monkey Cliff Booth watches made?
Every Cliff Booth watch is hand-built in Los Angeles using premium heavy-weight leather and stainless steel hardware.
What makes the Cliff Booth watch different?
The Cliff Booth watch combines film history, handcrafted leather construction, vintage military-inspired design, premium materials, and Red Monkey’s signature wide leather cuff style.
Hand-built in Los Angeles. Worn on screen. Built to become a legend.
Red Monkey Designs • Since 1995
FAQs
Yes. Red Monkey straps have been worn by touring artists and professional musicians across rock, country, metal, pop, and blues. Most recently, Lady Gaga, Shakira have called on Red Monkey for their tours.
Check out our ARTISTS page for some of our clients.
Red Monkey guitar straps have been hand-built for over 30 years right here in Los Angeles using premium full-grain leather and stage-ready hardware.
Wider straps tend to be preferred for heavier guitars and basses because they spread weight across the shoulder. We use very heavy leathers so a wider strap may actually create more shoulder drap when playing for long periods of time.
Narrow straps are great for lighter guitars and vintage style. Slash and Joe Perry, however, like the SLASHER guitar strap for their heavy Les Pauls.
Leather guitar straps are preferred by many players because they are strong, comfortable, long-lasting, and have a classic stage look. Red Monkey straps are made from 100% full-grain leather for premium durability and feel.
The best guitar straps combine comfort, durability, proper width, reliable hardware, and quality materials. Full-grain leather is one of the strongest choices because it breaks in over time while staying durable for years of playing.
Check our SIZING CHART to get the best results.
Most times, we DO NOT recommend using your current pant sizing or another companies belt sizing.
If you're unsure what size strap you need, email us and we'll help guide you through the process of choosing the best size for your height and weight and where the guitar hangs on your body. You can email: rmonkey@redmonkeydesigns.com
Yes, if you need something longer or shorter, simply put your sizing request into the ORDER NOTES section during checkout and we'll take it from there.
Strap locks are a specialty quick release system that many gigging musicians use. They not only help secure your strap to your guitar, they allow for quick release and changing of guitar straps. Many locking systems (e.g.. Dunlop, Schaller, Grover) have a slightly larger diameter hole for mounting. While our traditional guitar strap mounting hole will allow for mounting, we offer to punch the hole larger to make fitment of strap locks easier.
All our gear is HAND-BUILT to order. We generally ask for about 5-7 build days before shipping. Usually we ship more quickly and other times we need a tad more time. We appreciate your patience during our building process.
Due to the hand-built nature of our gear, we do not except returns for refunds. We want all our clients to be happy with their gear purchase. With that said, hand-built goods take time and extra labor to complete so we ask that you be sure to take extra care when ordering. Should you need to return an item, we gladly offer exchanges and or store credit toward future purchases.
If we've not started building your order, we will gladly cancel your order. Please let us know as quickly as possible after placing your order.