14 Oldest Rolex Watches Ever Made

Rolex is one of the most iconic and well-known watch brands in the world, with a history dating back over a century. Throughout its long and illustrious history, Rolex has produced a wide range of timepieces, each with its own unique style and features. However, there are certain Rolex watches that stand out for their age and historical significance. These timepieces are not only valuable collectors’ items but also fascinating glimpses into the past, capturing the style and technology of their era.

In this blog, we will take a look at the oldest Rolex watches ever made, tracing the evolution of this iconic brand and showcasing some of its most impressive and historic timepieces. From the early days of Rolex to the modern era, these watches represent a true testament to the enduring legacy of this legendary brand.

14. Yacht-Master

photo source: LUCERNE

The watch was first introduced in 1992, and since then, it has undergone several upgrades and iterations. The Rolex Yacht-Master is designed for use in sailing and other nautical activities. It is known for its sporty, yet elegant design, which includes a distinctive rotatable bezel with raised numerals and graduations, as well as a large, easy-to-read dial. The watch is also water-resistant to a depth of 100 meters, making it suitable for diving and other water sports.

The watch is powered by Rolex’s proprietary self-winding mechanical movement, which is known for its accuracy and reliability. One of the most distinctive features of the Yacht-Master is its rotatable bezel. The bezel is designed to help sailors keep track of the elapsed time during a race or other nautical activity. The bezel is made from a variety of materials, depending on the specific model, including Cerachrom (a type of ceramic), gold, and platinum.

Did You Know?

The Yacht-Master features Rolex’s patented Oyster case, which is designed to be highly water-resistant and durable. The case is made from a solid block of metal and features a screw-down crown, which helps to prevent water from entering the watch.

13. Sea-Dweller

photo source: Chrono24

The Sea-Dweller is a popular choice among professional divers and enthusiasts who demand the highest level of performance from their equipment. Its combination of durability, accuracy, and water-resistance make it one of the most sought-after diving watches on the market.

The Rolex Sea-Dweller was originally developed in collaboration with diving professionals and was designed to meet the needs of commercial and military divers. The watch is known for its rugged construction and high level of water-resistance, which make it ideal for use in extreme diving conditions.

The Sea-Dweller is equipped with a helium escape valve, which is designed to allow any helium gas that may have entered the watch during deep-sea diving to be safely released during decompression. The valve helps to prevent the crystal from popping off the watch due to the pressure differential between the inside and outside of the watch during ascent.

Did You Know?

The Sea-Dweller features Rolex’s proprietary Chromalight display, which is designed to provide exceptional visibility in low-light conditions.

12. Cosmograph Daytona

photo source: LUCERNE

The Rolex Cosmograph Daytona is a highly sought-after chronograph watch that was first introduced in 1963. The watch is named after the famous Daytona International Speedway in Florida, which is known for its high-speed racing events. The Daytona is designed to meet the needs of professional racing drivers and enthusiasts, and it has since become an iconic timepiece in the world of motorsports.

The Daytona is known for its elegant design and advanced functionality. The watch features a tachymetric scale on the bezel, which allows the wearer to measure speed over a specific distance. The chronograph function allows the wearer to time intervals with extreme accuracy, making it a useful tool for measuring lap times during a race.

Did You Know?

The Daytona is powered by Rolex’s proprietary self-winding mechanical movement, which is known for its accuracy and reliability. The movement is also COSC-certified, which means that it has been tested and certified to meet the highest standards of accuracy and precision.

11. Deep Sea Special

photo source: Hodinkee

The Rolex Deep Sea Special is a historic diving watch that was designed to withstand the extreme pressure of deep-sea exploration. The watch was first introduced in 1960 and was used in the groundbreaking Trieste dive to the bottom of the Mariana Trench in 1960, which was the deepest dive ever recorded at the time.

The Deep Sea Special was designed with a unique pressure-resistant case that could withstand depths of up to 10,916 meters (35,800 feet). The watch was equipped with a specially designed crystal that was nearly an inch thick and made from a material called “Plexiglas,” which was chosen for its ability to withstand the extreme pressure at the bottom of the ocean.

Rolex has continued to develop its deep-sea diving watches since the introduction of the Deep Sea Special. Today, the brand’s Deepsea model is designed to withstand depths of up to 3,900 meters (12,800 feet) and is equipped with a helium escape valve and a special bracelet extension system to accommodate diving suits.

Did You Know?

The Deep Sea Special also featured a unique “hockey puck” design, with a flat and wide case that allowed the watch to withstand pressure from all directions. The watch was not designed for regular use, but rather for special missions and scientific expeditions.

10. Oyster Perpetual Milgauss

photo source: LUCERNE

The Rolex Oyster Perpetual Milgauss is a unique watch in the Rolex lineup that was originally designed for scientists and engineers who worked in environments with high levels of magnetic fields. The watch was first introduced in 1956 and was named “Milgauss” (a combination of “mille” for thousand and “gauss” for a unit of magnetic flux density) to reflect its ability to resist magnetic fields of up to 1,000 gauss.

The Milgauss has gone through several design iterations over the years, with the latest version featuring a 40mm case and a caliber 3235 self-winding mechanical movement that is known for its precision and reliability. The watch is available in several different versions, including models with black or white dials, and with either a steel or steel and gold bracelet.

Did You Know?

The Milgauss is known for its distinctive design, with a unique lightning bolt-shaped second hand and a green-tinted sapphire crystal. The watch also features a Faraday cage, which is a special antimagnetic shield that protects the movement from magnetic fields.

9. Day-Date

photo source: LUCERNE

The Rolex Day-Date is one of Rolex’s most iconic and prestigious models. Introduced in 1956, it was the first wristwatch to display the day of the week spelled out in full and the date on the dial. The Day-Date quickly became a favorite among world leaders, CEOs, and other prominent figures, earning it the nickname “President’s Watch.”

The Day-Date is known for its elegant and classic design, featuring a 36mm case in either yellow, white, or rose gold, as well as platinum. The watch is also available in a range of dial colors and styles, including a variety of diamond-set options. The most distinctive feature of the Day-Date is the “President” bracelet, which is made up of three semi-circular links and is only available on the Day-Date.

Did You Know?

Over the years, the Day-Date has been worn by many prominent figures, including U.S. Presidents such as Lyndon B. Johnson, Ronald Reagan, and Bill Clinton, as well as other world leaders, actors, and musicians.

8. GMT-Master

photo source: Mamic 1970

The Rolex GMT-Master was initially designed in collaboration with Pan American Airways for their pilots to keep track of multiple time zones, and was first introduced in 1954. The GMT-Master features a 24-hour hand and a rotating bezel with a 24-hour scale, allowing the wearer to track two different time zones at once. The first models were equipped with a bakelite bezel insert, but this was later replaced with an aluminum insert in the 1960s, and then with a ceramic insert in the 2000s.

The Rolex GMT-Master has undergone several updates and variations over the years, including the GMT-Master II which was introduced in 1983 and featured an independent quickset hour hand and a modified movement. Today, the GMT-Master II is available in various materials, such as stainless steel, gold, and platinum, and features a variety of dial and bezel color combinations. It remains a popular choice among both pilots and watch enthusiasts.

Did You Know?

Rolex also produces a GMT-Master II “Pepsi” model, which features a blue and red ceramic bezel insert, and a GMT-Master II “Batman” model, which features a blue and black ceramic bezel insert.

7. Turn-O-Graph

photo source: SwissWatchExpo

The Turn-O-Graph was the first Rolex watch to feature a rotating bezel with a graduated scale, which allowed it to be used as a timing device. The watch was initially marketed towards pilots, but its unique design and functionality also appealed to the general public. It features a 36mm case, a stainless steel or gold bezel with a variety of different colored inserts, and a steel or gold bracelet.

The watch is also equipped with a date function, and is powered by the Rolex Calibre 3135 self-winding movement. In the 1960s, the Turn-O-Graph underwent a redesign, which included a larger case size and a more pronounced rotating bezel. However, the watch was eventually discontinued in the 1970s, before being reintroduced in 2005 as part of the Rolex Datejust line.

The Turn-O-Graph has been worn by several famous individuals, including Elvis Presley and Dwight D. Eisenhower. The latter was given a special Turn-O-Graph by Rolex in honor of his presidency.

Did You Know?

It is also known as the “Thunderbird” due to its association with the United States Air Force Thunderbird aerobatic team, who were gifted Turn-O-Graph watches by Rolex in the 1950s.

6. Explorer

photo source: Worn & Wound

The Rolex Explorer is a legendary watch that has become an iconic symbol of adventure and exploration. It was designed specifically for use by mountaineers, explorers, and other adventurers who needed a reliable and accurate timepiece for use in extreme environments.

The Explorer was first introduced in 1953, and was inspired by Sir Edmund Hillary and Tenzing Norgay’s successful ascent of Mount Everest earlier that year. The watch was designed to withstand extreme temperatures, high altitudes, and other harsh conditions, making it an ideal choice for those who venture into the unknown.

The original Rolex Explorer featured a 36mm case, a black dial with large, luminescent numerals, and a rugged stainless steel bracelet. It was also equipped with a self-winding movement, a screw-down crown, and a shatter-resistant crystal, all of which helped to make it one of the most durable and reliable watches of its time.

Did You Know?

Despite its many updates and variations, the Rolex Explorer remains true to its original purpose as a rugged and reliable timepiece for adventurers and explorers. Its classic design and functionality make it a popular choice among collectors and enthusiasts, who appreciate its rich history and iconic status as one of the world’s most beloved watches.

5. The Submariner

photo source: Time+Tide

The Rolex Submariner is a well-known and highly respected diving watch that was first introduced in 1953 for professional divers. It is a very sturdy and dependable watch that can withstand depths of up to 300 meters. The original design of the Submariner featured a black dial with large luminescent hour markers and hands, and a self-winding movement for precise timekeeping.

The Submariner is beloved by watch enthusiasts and collectors for its bold hour markers, clean lines, and iconic Rolex logo, and is widely considered to be one of the most recognizable and sought-after timepieces in the world. It has a rich history and has remained true to its original purpose as a reliable and accurate timepiece for divers, cementing its status as one of the most respected and sought-after watches in the world.

Did You Know?

The watch features a unidirectional rotating bezel that allows divers to track their time underwater, as well as a screw-down crown and caseback that help to ensure the watch remains water-resistant.

4. Datejust

photo source: Chrono24

The Rolex Datejust is a classic and iconic watch that has been a mainstay of the Rolex collection since its introduction in 1945. The Datejust is renowned for its timeless design, precision, and reliability, and is a symbol of luxury and status.

The watch’s case and bracelet are crafted from high-quality materials such as stainless steel, 18k gold, and two-tone combinations. The watch is also available in a range of dial colors and materials, including mother-of-pearl, diamond-set, and classic champagne.

Datejust has undergone several updates and variations, including the addition of a fluted bezel and the use of materials such as Rolesor, a combination of stainless steel and gold. The watch has also been worn by many influential figures, including US President Dwight D. Eisenhower.

Did You Know?

The Datejust features a date display at the 3 o’clock position, which is magnified by a Cyclops lens for easy reading. The watch is available in a range of sizes, including 31mm, 36mm, and 41mm, making it suitable for both men and women.

3. Bubbleback

photo source: British GQ

The Rolex Bubbleback, also known as the Rolex Oyster Perpetual Bubbleback, is a vintage Rolex watch that was produced from the 1930s to the 1950s. It is called the Bubbleback because of the distinctive bulge on the back of the watch, which accommodates the rotor of the self-winding movement. The Bubbleback was one of the first watches to feature a fully automatic movement, which wound the mainspring through the motion of the wearer’s wrist. The movement was also equipped with a Breguet hairspring, which improved accuracy and durability.

It was also the first Rolex watch to feature a winding rotor that pivoted on a ball bearing, which improved winding efficiency and reduced wear on the movement. The Bubbleback was produced in large numbers and was a popular choice among watch buyers during its production period. It was marketed as a high-quality, reliable timepiece that was suitable for everyday wear.

The Bubbleback is highly collectible today and is prized for its vintage charm, distinctive design, and exceptional craftsmanship. Some models, such as the rare “Doctor’s Watch” with a pulsometer scale, can command high prices at auction.

Did You Know?

The Bubbleback was the first Rolex watch to feature a screw-down caseback, which improved water resistance and dust protection.

2. Prince

photo source: SwissWatchExpo

The Rolex Prince is a vintage watch model that was first introduced in 1928. It was a departure from the round watch cases that were popular at the time, featuring a rectangular case with an elongated shape that was designed to fit more comfortably on the wrist.

The Prince was also notable for its precision movement, which featured a large, highly visible balance wheel that was regulated by a Breguet hairspring. This movement was known as the Rolex Calibre 300, and it was highly accurate for its time, earning it the nickname “the doctor’s watch” because it was frequently used by medical professionals to time patients’ pulses.

The Prince was also notable for its innovative movement design, which featured a “butterfly” rotor that wound the mainspring in both directions. This design helped to improve winding efficiency and reduce wear on the movement.

Did You Know?

The Rolex Prince was originally marketed as a luxury watch, and it was priced higher than many other watches of its time. It was often sold to wealthy customers and was a popular gift among the European aristocracy.

1. Oyster Perpetual

photo source: Rolex

Rolex’s first watch was the Oyster Perpetual, which featured waterproof and self-winding functionalities. The Oyster Perpetual is characterized by its classic and timeless design, featuring a simple and elegant dial with a date display and the iconic Rolex crown logo. The “Oyster” part of the name refers to the patented Rolex case design that is water-resistant and dust-resistant, originally introduced in 1926. The “Perpetual” part refers to the self-winding movement that powers the watch, which was introduced by Rolex in 1931 and is still used in the Oyster Perpetual today.

The Oyster Perpetual line includes a wide range of models in various sizes, materials, and colors, including the Datejust and Day-Date models. It is known for its precision, durability, and reliability, and is a popular choice among watch enthusiasts and collectors around the world.

Did You Know?

The Oyster Perpetual has been worn by numerous celebrities and world leaders over the years, including Winston Churchill, Martin Luther King Jr., and Roger Federer.