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The Most Beautiful Vintage Rolex Watches Ever Sold at Auction

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Rolex is a brand that needs no introduction. Even if you are not interested in horology and have never owned a watch, chances are you have still heard the name Rolex and know that the iconic company produces some of the best timepieces in the world. So what makes this Swiss luxury brand stand out from its counterparts?

“Rolex makes watches that work very well,” summed up Paul Boutros, Americas' Head of Watches at Phillips, the auction house that has sold some of the most expensive Rolex timepieces. “So they really understand how to make a watch fit wrists of all sizes very, very well, and that's not an easy thing to do across their product line. […] to make a watch that works well and fits well and looks good—that's difficult.”

And Rolex has consistently excelled in all of the above, which is one of the reasons why its vintage timepieces command such large sums of money at auctions.

“They appeal to today's collector sensibilities. They're sized perfectly for today's tastes. The Day-Date is 36 millimeters, vintage Submariners range in size from 37 millimeters to 40 millimeters. Daytona's are 37 millimeters to today at 40 millimeters, and the size of these watches from the ‘50s, ‘60s, ‘70s, ‘80s—they're very relevant for today's tastes,” Boutros added.

Quality is also a factor, of course. Rolex watches are simply “built tough,” as Boutros put it. The company produces all of its pieces—from casting the gold alloys to the assembly of the movement and the case—in-house. The process ensures that every single Rolex watch is up to the company’s rigorous standards.

“If you hit [a Rolex watch] against your desk, if you hit it against the doorknob, it's really no big deal,” Boutros said.

He also explains that while most watches usually have three-to-four registered bidders, Rolex’s vintage sports timepieces usually have between six-to-eight. The record, of course, belongs to the king of all Rolex watches—Paul Newman’s Daytona that was sold in 2017 and had 34 registered bidders ahead of the auction.

So, without further ado, here are the most beautiful (and expensive) Rolex watches that have ever gone under the hammer, as it were.

Rolex Paul Newman Daytona Ref. 6239

Sold for: $17,752,500 in 2017

The dream of any watch collector would be to own this exact Rolex Paul Newman Daytona produced in 1968. It is the first Rolex Daytona watch fitted with an “exotic dial.” It also has a tachymeter bezel and features a personal engraving by Newman’s wife that reads, “Drive Carefully, Me” on its stainless steel case-back.

Rolex Cosmograph Daytona ref. 6265 “The Unicorn”

Sold for: $6,132,618 in 2018

This exquisite chronograph is the only Daytona of its kind (hence its nickname). It is entirely crafted in white gold and sports a black dial and a bark-finished bracelet. It was owned by John Goldberger, one of the most prominent collectors in the world, who sold it to raise funds for charity, explains Boutros.

Rolex ref. 6062

Sold for: $ 5,232,479 in 2017

This superbly-preserved, 18-karat yellow-gold automatic Rolex was previously owned by Vietnamese emperor Bao Dai. It has a triple calendar with moon phase dial that is also set with diamonds at 12, 3, 5, 8, and 10 o’clock. Rolex only produced that triple calendar and moon phase watch for a couple of years starting in 1950 before it re-introduced them again in 2016.

Rolex Cosmograph Daytona, ref. 6263 “The Legend”

Sold for: $3,844,312 in 2017

This 18-karat yellow gold Oyster Cosmograph "Paul Newman," aka The Legend, is one of only three known similar watches on the market. Its most fascinating feature is the dial—a “creamy lemon shade,” as Phillips put it in its catalog—in sharp contrast with the ivory dials that were fitted to stainless steel Paul Newmans at the time.

Rolex Cosmograph Daytona, ref. 6240 – “The Neanderthal”

Sold for: $3,111,497 in 2018

Produced for a few years only around 1965, this is the first “Cosmograph” wristwatch equipped with screw-down chronograph pushers for improved water resistance. Its unique black and white dial features oversized registers and black outer seconds marks set against a white track.


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