7 “Grail Worthy” Vintage Rolex Watches

some of the best Vintage Rolex watches worth the hunt and investment

Collecting vintage Rolex watches, like many similar higher end pastimes, can be somewhat of a slippery slope, but a greatly enjoyable one at that.

In many cases, after new collectors get their feet wet in the vintage Rolex market with something like a standard Ref. 5513 Submariner, for example, they find themselves looking for more unique and rarer examples when it comes time for their next timepiece.

DON’T MISS: 10 Things To Understand Before Buying a Vintage Rolex

For those looking to invest their time and money into the most desirable and coveted vintage Rolex references that are still in existence today, we’ve picked our Top 10 vintage Rolex watches worthy of what true aficionados elevate to “grail status”.

Without further ado, let’s begin.

‘Paul Newman’ Daytona

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In every important watch collection, you’re bound to find at least one Rolex Daytona. Which should come as no surprise, given the unparalleled history and erudition that surrounds this legendary chronograph. If you happen to be in the market for one of these, and a conventional example just won’t do, the ‘Paul Newman’ Daytona is the way to go.

best vintage rolex investment

The iconic photo of Paul Newman wearing a Rolex Daytona. Image via Jake’s Rolex World.

Why is it referred to as the ‘Paul Newman’ Daytona? As the story goes, after Italian collectors noticed a Ref. 6239 featuring the exotic dial on the actor’s wrist in a notable photograph (shown above), they began to refer to it simply as the Paul Newman. And the rest, as they say, is history.

Ref. 6542 GMT Master

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To this day, one of the most popular sports models in the Rolex lineup is the GMT Master. Designed with jet-setting individuals and professional pilots in mind, the Ref. 6542 was introduced in 1954, and stunned watch buyers with its vibrant red and blue, ‘Pepsi’-colored, bakelite bezel. Combine that with a clean, glossy gilt dial, and a either a Jubilee or Oyster bracelet, or even an aftermarket leather strap as pictured above, and you’ve got an incredibly good-looking specimen.

Ref. 6541 Milgauss

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When they introduced their first Milgauss in 1956, Rolex truly cemented the fact that they produced watches for professionals in nearly every field. In the case of the Milgauss, Rolex targeted the scientific community, as the watch featured an internal Faraday cage that could protect the movement from strong magnetic fields. The watch was also rather easy on the eyes, which didn’t hurt either, with it’s distinctive lightning bolt seconds hand.

Military Submariner

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Although all vintage Submariners do possess an indescribable rugged charm, few standard issue Submariners are as impressive on the wrist as the Ref. 5517 and 5513/5517 military Submariners. Issued exclusively to enlisted members of the British military, these fixed bar dive watches are commonly regarded as some of the ultimate tool watches. They are also, quite possibly, some of the rarest Submariners ever made.

“Stella” Dial Day-Date

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Characterized by their bold, and often brightly colored dials, the “Stella” Day-Dates are yet another example of how Italian collectors have influenced the way certain Rolex models become known across the globe.

Since these exciting dials were known to glimmer under light, collectors began calling them ‘stella’, which means star in Italian. Rolex manufactured these dials in many colors, including green, pink, blue, yellow, and orange, so there really is a “Stella” dial Day-Date out there for everyone.

Space Dweller

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The earlier Rolex Explorers are seen by many important collectors as some of the ultimate tool watches ever produced by Rolex. And while it could be said that the most interesting references in the line pre-date the Ref. 1016, there is one 1016 that might challenge this notion.

The watch I speak of is, of course, the Space Dweller. The Space Dweller is an ultra rare dial variant of the Explorer that Rolex produced to capitalize on the popularity of the Project Mercury astronauts’ 1963 visit to Japan. These watches were produced specifically for the Japanese market, and are highly collectible today.

“Patent Pending” Double Red Sea Dweller

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Early on in the production of Rolex’s most distinguished dive watch, the Sea Dweller, some examples featured the words “Patent Pending” on the caseback. These two words make all the difference when it comes to putting a value on this watch, as “Patent Pending” examples have become exceedingly rare and sought after, if not coveted.

Interest to note, is that the “Patent Pending” designation is not peculiar to the Sea Dweller. It’s not uncommon to find the marking on pieces with military provenance, as many of these early Sea Dwellers were originally purchased by professional divers as tool watches.

Thanks for reading.

Stylishly Yours,

Paul Altieri
He Spoke Style

Paul Altieri is the Founder and CEO of the popular pre-owned watch site Bob’s Watches.

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