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Men’s Luxury Watches: 5 Iconic Classics

Paul Altieri

What makes a luxury watch a classic? Some would say a rich history and a successful production run. Many also consider a timeless style that supersedes current-fashion trends a trademark of any watch icon. The watches listed in our Top 5 guide of the most iconic and classic luxury watches all fit the bill, with production runs that span decades and timeless, unwavering designs.

Mens Luxury Watches 5 Iconic Classics Patek Philippe Nautilus
What are the most iconic luxury watches of all time?

Rolex Datejust

Mens Luxury Watches 5 Iconic Classics Rolex Datejust

Even if you’re new to collecting luxury watches, chances are that you know of the Rolex Oyster Perpetual Datejust. The Datejust debuted in 1945 and continues to remain in production today, making it one of Rolex’s oldest and most successful models. Its design is absolutely timeless and features highly versatile proportions, a convenient self-winding movement with a jumping date display, and a waterproof case. This watch is suitable for daily wear, yet it’s incredibly easy to dress up. Its versatility is a major selling point among many collectors, as is its attractive price point.

The Datejust was the first wristwatch to offer an automatically changing date display on its dial. It has made appearances on the wrists of many influential men and women throughout its history, including former President Dwight D. Eisenhower, Paul Newman in the film The Color of Money, and international tennis champ Roger Federer.


Patek Philippe Nautilus

Mens Luxury Watches 5 Iconic Classics Patek Nautilus

The Patek Philippe Nautilus was designed by legend Gerald Genta. That fact alone makes it a classic in the vast world of luxury watches. But what also makes this wristwatch a favorite among many collectors is its unique feature set. From the design of the noncircular bezel to the stunning Teak-inspired dial, the Nautilus draws much inspiration from boating and sailing and is often associated with high class and wealth. Many luxury watch enthusiasts also appreciate its slim profile and elegantly-tapered integrated bracelet. The Nautilus is every bit an elegant luxury watch as it is a reliable timekeeper while exploring the vast ocean.

The collection is available in several metal options, with stainless steel being the most coveted and difficult to find. It can also be found on a leather bracelet or with a stunning diamond-encrusted bezel on the ladies’ models. As it goes with many Patek watches, the Nautilus will require a serious investment. However, if you can afford to add one to your watch box, it’s more than worth the price.


Panerai Luminor

Mens Luxury Watches 5 Iconic Classics

In 1949, Panerai replaced the radium-based material on their dials with a Tritium-based material, which they patented as “Luminor”. A year later, the iconic Luminor 1950 case with its oversized crown guard and cushion-shaped case, was developed and the Panerai Luminor as we know it was born. Its history as an Italian Navy tool watch, coupled with its timeless style, has made the Panerai Luminor a favorite among collectors since it became commercially available in the 1990s.

What’s also fascinating about the collection is that it keeps many of the design elements as the original Navy tool watch from the 1950s while also including many modern upgrades, such as improved lume and new in-house movements.  The Luminor is often viewed as one of the most robust luxury watches currently available, and is worn by everyone from watch enthusiasts to professional explorers. If you have the wrist size to wear it, we highly recommend investing in at least one of these iconic timepieces.


Omega Speedmaster

Mens Luxury Watches 5 Iconic Classics Omega Speedmaster Professional Moonwatch

Lovingly referred to as the “Moonwatch” and “Speedy”, the Omega Speedmaster has been a long-time favorite among luxury watch collectors in-the-know. Buzz Aldrin wore a Speedmaster strapped to the outside of his suit when he took his first steps on the moon, earning the watch its iconic nickname and making it a cult classic. The collection is varied. However, the Speedmaster’s core design remains the same with a tachymeter bezel and a reliable chronograph movement.

Omega is proud of its part in the first lunar landing and continues to release new editions of the beloved Speedmaster, making it one of the most obtainable luxury watches on our list. If you’re in the market for a chronograph wristwatch with enduring style and one of the most remarkable heritages around, then the Omega Speedmaster is the watch to get.


Breitling Navitimer

Mens Luxury Watches 5 Iconic Classics Breitling Navitimer

The Breitling Navitimer is distinguished by its slide rule bezel, which was a true innovation of its time. The rotating bezel aligns with a fixed scale on the periphery of the dial to determine various stats while in flight, such as climbing speed, distance traveled, and fuel consumption. While it was developed for aeronautical use, the Navitimer has since become a coveted timepiece among many luxury watch collectors. It’s also worth noting that not very many brands produce wristwatches with a slide rule function, which is why the Navitimer remains such a classic and desirable watch.

Functionality aside, the Navitimer enjoys immense success for its bold aesthetic. The case is robust and includes distinctive chronograph pushers and a sporty dial. If you desire a classic luxury watch that will get you noticed, the Navitimer is an excellent option to consider and a true icon within the industry.

Paul Altieri