17 of the World’s Most Expensive and Iconic Watches: Tom Brady’s Rolex ‘Player Special,’ Princess Diana’s Cartier Ticker and More Worth Millions

From diamond-encrusted watches to classically constructed timepieces, the practical accessory that sits neatly upon one’s wrist can sit at extravagant price points.

High-profile brand collaborations throughout 2023 have been part of the synergy that boosted sales in the watch industry. The same effect is produced when a celebrity’s image is attached to a product, like fine jewelry, which explains the high values of several timepieces listed below. Resellers are also enjoying the rewards of the wave.

WWD has listed some of the world’s most iconic timepieces that have been sold for lavish prices. Below, a roundup of striking designs with remarkable stories.

John F. Kennedy’s 14-karat gold Nastrix Timepiece, $120,000

Antiquorum sold John F. Kennedy’s 14-karat gold Nastrix timepiece in a New York auction for $120,000 on March 5, 2009. After Kennedy’s assassination, the watch was given to his widow, Jacqueline Kennedy, who later gifted it to her second husband, Aristotle Onassis.

Audemars Piguet Royal Oak Perpetual Calendar “John Mayer” Limited Edition Timepiece, $180,000

The limited edition Audemars Piguet Royal Oak Perpetual Calendar “John Mayer” timepiece is equipped with the manufacturer’s self-winding Calibre 5134. The 18-karat white gold watch’s design centers around the dial, which is finished in a sparkling blue faux crystal and adorned with an embossed night sky motif.

Omega Seamaster Planet Ocean Skyfall 007 Timepiece, $200,659.65

Omega auctioned the Omega Seamaster Planet Ocean Skyfall 007 timepiece through Christie’s on Oct. 5, 2012, for $200,659.65. Daniel Craig wore the watch during his turn as James Bond in the movie “Skyfall.”

Jackie Kennedy’s Cartier Tank Française Watch, $379,500

Kim Kardashian paid $379,500 for Jackie Kennedy’s Cartier Tank Française watch through a Christie’s auction in New York on June 21, 2017. The timepiece was originally gifted to Kennedy by her brother-in-law, Prince Stanislaw “Stas” Radziwill. 

John F. Kennedy’s Omega Ultra Thin Reference OT3980 Dress Watch, $420,000

The Omega Museum of Bienne, Switzerland, paid $420,000 for John F. Kennedy’s 18-karat gold Omega Ultra Thin Reference OT3980 dress watch through a 2005 auction in New York. The watch was given to Kennedy by his friend Grant Stockdale leading up to the 1960 presidential election.

Steve McQueen’s Heuer Monaco Watch, $500,000 – $ 1 Million

The Heuer Monaco watch worn by Steve McQueen while filming the 1971 classic “Le Mans” is the centerpiece of Sotheby’s Important Watches Auction, which will go on sale on Dec. 11. The watch has an estimated price of $500,000 – 1 million, according to the auction house.

“As a lifelong lover of the Heuer brand, it is a career highlight for me to be involved in bringing one of the most important watches in the history of the marque to auction. The connection between cars and watches is well-known, but the reference 1133B encapsulates this union in a way unmatched by other timepieces. For enthusiasts of racing, McQueen, or vintage chronographs, this watch represents the ultimate addition to any collection—a true ‘end game’ piece,” said Geoff Hess, Sotheby’s global head of watches.

The watch is one of six Heuer Monaco models with a blue dial sent to the “Le Mans” set. Within the six reference 1133B models, two were fitted on stainless steel bracelets and four with leather straps as worn by McQueen in the movie. Launched in 1969, the Heuer Monaco was among the first commercially available automatic chronograph wristwatches, introduced alongside the revolutionary Calibre 11.

Jean-Claude Killy’s 1951 Rolex Dato-Compax Chronograph Watch, $614,500

Auction house Antiquorum sold Olympic skiing champion Jean-Claude Killy’s 1951 Rolex Dato-Compax Chronograph watch for $614,500 in December 2012. For more than four decades, Killy acted as a Rolex ambassador.

Tom Brady’s Rolex Reference 6241 Daytona Paul Newman ‘John Player Special,’ $1.1 Million

Tom Brady originally wore the Rolex Reference 6241 Daytona Paul Newman “John Player Special” watch at the beginning of the 2023 football season. The watch was spotted during a commemorative ceremony at Gillette Stadium, at which the New England Patriots honored Brady during the team’s home opener against the Philadelphia Eagles. The design features a yellow gold chronograph wristwatch with bracelet. The watch was sold at auction for a whopping $1.1 million at Soethby’s.

Amelia Earhart’s Patek Philippe, $1.8 million

Amelia Earhart’s one-of-a-kind Patek Phillip sold for over $1.8 million at Monaco Legend Group’s Exclusive Timepiece Auction on April 23. The Patek was originally ordered by Harry Gordon Selfridge, founder of the London-based Selfridges department store, in 1928 and gifted to the record-breaking land and sea racer, Sir Henry Seagrave. After a boating accident killed Seagrave, the watch was returned to Selfridge, who gifted the piece to Amelia Earhart.

Titanic Memorabilia Time Piece, $1.97 million

This 18k gold pocket watch was a gift from survivors of the Titanic maritime tragedy to the captain of the R.M.S. Carpathia, the ship that rescued surviving Titanic passengers. The watch was acquired at auction in the United Kingdom by Tiffany & Co. for $1.97 million, making the time piece the highest-valued artifact of Titanic memorabilia ever sold.

Eric Clapton’s Patek Philippe Ref. 2499/100 Watch, $3,635,808

In a Geneva auction, Christie’s sold a rare 1987 Patek Philippe Ref. 2499/100 watch from the personal collection of guitarist Eric Clapton for $3,635,808 on Nov. 12, 2012. The timepiece features 23 jewels, a silvered matte dial, an applied gold baton and gold dauphine hands.

Emperor of China’s Patek Philippe Ref. 96 Quantieme Lune Timepiece, $6.2 million

A Patek Philippe Ref 96 Quantieme Lune watch that once belonged to the last emperor of China’s Qing Dynasty, Aisin-Gioro Puy, sold at a Phillips Hong Kong auction for $6.2 million in May 2023. The timepiece features an intricate face adorned with a small moon phase painting.

Prince Mohammed Tewlik A. Toussou’s Patek Philippe Ref. 1518 Watch, $9.57 million

In a New York auction, Sotheby’s sold a Patek Philippe Ref. 1518 watch belonging to Prince Mohammed Tewlik A. Toussou for $9.6 million in December 2021. While almost 300 models of the watch were originally produced, only one-fifth of them were released in pink gold, with the majority in yellow gold. 

Jacob & Co. Yellow Diamond-Encrusted Watch, $20 million