A Rolex watch is a great way to splash some cash and show the world your discerning taste. The brand’s designs range from classic and elegant, through to brave and blingy. As such, no matter your taste, there’s an option for you. If you have a hankering to treat yourself to the ultimate in luxury timepieces, then this list of the most expensive Rolex watches is the perfect place to look for inspiration.

1. Submariner Automatic Chronometer Diamond Silver Dial Men’s Watch

If you’re a gent who loves their Rolex watches iced out, then this is the perfect luxury choice for you. The 18kt white cold case boasts a blue diamond-set bezel and hour markers. The band is also 18kt white gold, complete with plenty of extra paved bling. In terms of functionality, there’s a date display, Rolex caliber 3135 automatic movement, and an oysterlock clasp. Being one of Rolex’s Submariner designs, an industry-leading dive watch, it’s water-resistant to 1000 feet. Plus, the face features a scratch-resistant sapphire crystal, so you don’t need to worry about anything dulling your shine.
BUY $230,000

Submariner Automatic Chronometer Diamond Silver Dial Men's Watch


2. Pearlmaster 39 Men’s 18kt Everose Gold Pearlmaster Diamond Pave Watch

The Pearlmaster 39 Rolex watch is the ultimate presentation of exquisite design and style. There is just so much to be awed by in this watch. The sophisticated five-link everose Pearlmaster bracelet is set with diamonds that sit into hand-carved seats for perfect placement. Then, there’s even more bling with the dial boasting a massive 713 diamonds, while the bezel is set with even more precious stones. Roman numerals mark the hour, for a unique approach to numbering. Meanwhile, the everose is a patented color of 18kt pink gold alloy, exclusive to Rolex. This watch is the perfect choice for daring men, who are unafraid of asserting their style.


BUY: $174,300

Pearlmaster 39 Men's 18kt Everose Gold Pearlmaster Diamond Pave Watch

3. GMT-Master II Automatic Diamond Men’s Watch

Wrap this stylish GMT-Master II around your wrist and wait for the compliments to roll in. This watch features a three-link 18kt gold bracelet that closes with Rolex’s safe and secure Oysterlock clasp. The 40mm case is 18kt rose gold and boasts a bi-direction rotating bezel. The bling is bold on this design, with 29 diamonds and 30 blue and red sapphires gracing the face, along with diamond pave hour markers. The Rolex caliber 3186 automatic movement keeps you punctual, while the date shows at 3 o’clock for easy reference. Initially designed for explorers and adventurers, the watch has dual time-zone functionality, so no matter where your travels take you, you can always check the time back home.


BUY: $163,000

Gmt Master Ii Automatic Diamond Men's Watch


4. Cosmograph Daytona Chronograph Automatic Chronometer Diamond Men’s Watch

Discover another luxury watch from the Cosmograph Daytona Range. This Rolex features an attractive navy blue leather band, complete with a tang clasp for gents who prefer a more traditional look. However, this design still features plenty of sparkly detail. The pave diamond dial also has diamond hour markers, while the tachymeter scale bezel is set with blue stones to coordinate with the band. You’ll find the chronograph dials are easy to read with clear white faces, while the luminescent hands make telling time easy, even in low light. Lastly, your watch will remain scratch-free thanks to the sapphire crystal scratch-resistant face.


BUY: $136,000

Cosmograph Daytona Chronograph Automatic Chronometer Diamond Men's Watch


5. Cosmograph Daytona Eye of the Tiger Chronograph Automatic Chronometer Diamond Men’s Watch

Take a walk on the wild side with Rolex’s Eye of the Tiger Cosmograph Daytona watch. The casing on this watch features 18kt gold, as well as a fixed diamond-set bezel. Tiger stripes, gold-tone hands, and diamond hour markers boldly decorate the dial. While the style could be over the top, the black Oysterflex rubber strap gives the watch a more youthful, athletic vibe, and balances out the style. The Cosmograph Daytona range was initially designed for professional race car drivers. Consequently, it features a chronograph with three sub-dials for 60 seconds, 30 minutes, and one hour. Plus, the caliber 4130 automatic movement enhances the watch’s reliability, ensuring you always arrive on time.


BUY: $130,000

Cosmograph Daytona Eye Of The Tiger Chronograph Automatic Chronometer Diamond Men's Watch


6. Day-Date 40 Diamond Pave with Red Sapphire Bezel Men’s Watch

The regal red and gold of this Day-Date 40 Rolex watch make it fit for kings. This prestigious watch design was launched in 1956. As well as the day, the fully lettered day of the week shows in the window at the top of the dial. Plus, it’s waterproof to 330 feet and has a new-generation caliber 3255 movement. In terms of aesthetics, you can’t get much grander. The triple-link President bracelet is made from 18kt yellow gold, while the diamond-paved dial has gold-tone hands. The bezel is encrusted with red sapphires, as are the Roman numeral hours. This is the kind of watch that exudes power and refinement.


BUY: $122,000

Day Date 40 Diamond Pave W Red Sapphire Bezel Men's Watch


7. Pearlmaster 39 Diamond Pave Dial Men’s 18kt Rose Gold Pearlmaster Watch

Select a more toned-down version of the full diamond Pearlmaster 39 with this rose-gold model. There’s still plenty of frosting to show off, though. It has the iconic five-link Pearlmaster bracelet, with diamonds on the 2nd and 4th channels, plus 713 diamonds on the dial, and more around the fixed bezel. The 18kt everose theme continues onto the hands as well as the Roman numerals that adorn the face. From a functional perspective, the case is waterproof to 300 feet and scratch-resistant. Meanwhile, the caliber 3235 keeps the time well, and the date is displayed at the 3 o’clock position.


BUY: $97,530

Pearlmaster 39 Diamond Pave Dial Men's 18kt Rose Gold Pearlmaster Watch


8. Oyster Perpetual Cosmograph Daytona Ice Blue Dial Automatic Men’s Chronograph Watch

If bling is not your thing, then go for a luxury Rolex watch like this Cosmograph Daytona with an ice-blue dial. The white platinum case complements the blue well, while the black ceramic bezel provides contrast. Additionally, diamonds mark each hour, while the three sub-dials show 60 seconds, 30 minutes, and 12 hours for the chronograph. Like other designs of the Cosmograph Daytona, the watch is waterproof and scratch-resistant. The sportslike styling makes this a brilliant choice for gentlemen on the go.


BUY: $92,750

Oyster Perpetual Cosmograph Daytona Ice Blue Dial Automatic Men's Chronograph Watch


9. Cosmograph Daytona Chronograph Diamond Black Dial Men’s Watch

Go for more classic styling with this diamond and black dial Cosmograph Daytona. This particular design has been on the market since 1963 and has stuck around because of its suave styling. Perfect for the office, the black leather strap and black dial pair well with a suit, without being ostentatious. The durability is excellent for daily wear, with scratch-resistant surface, screw-down crown, and fold-over safety clasp. Luxury details show in this Rolex watch through the combination of diamond and Arabic numeral hour markers. Plus, the bezel is set with 24 baguette diamonds, a subtle shape, yet just as sophisticated.


BUY: $79,650

Cosmograph Daytona Chronograph Diamond Black Dial Men's Watch


10. Day-Date 40 Blue Dial Automatic Men’s Platinum President Watch

Enjoy timeless styling with this Rolex Day-Date watch. Named for the fully-worded day displayed across the 12 o’clock position and the date at 3 o’clock, it’s an impressively practical face. Keep the time accurately with the automatic caliber 3255 movement, which contains 31 jewels. Next, the platinum case encompasses the royal blue dial with silver-toned hands and Roman numeral hour markers. Keep the watch safely secured to your wrist with the platinum President bracelet with a folding clasp. This is the kind of watch that’s the ultimate choice for a classy man who appreciated simple refinement.


BUY: $56,925

Day Date 40 Blue Dial Automatic Men's Platinum President Watch


11. GMT-Master II Automatic Chronometer Meteorite Dial Pepsi Bezel Watch

This GMT- Master II emulates its blingier counterpart, but with more subtle ornamentation. The combination of Pepsi red and blue coloring accents the bezel well. Meanwhile, the 18kt white gold case and oyster bracelet say understated luxury, as does the Mercedes branded sword, and Breguet-style hands. Quickly check the date on the dial through the sapphire crystal scratch-resistant face. It’s a timeless aesthetic that serves modern gents well.


BUY: $51,850

Gmt Master Ii Automatic Chronometer Meteorite Dial Pepsi Bezel Watch


12. Sky-Dweller White Dial Automatic Men’s 18kt Everrose Gold Oyster Watch

Travel the world with the Sky-Dweller Rolex watch. It’s both easy to use and technologically advanced. Perfect for the jet-set, it boasts an innovative annual calendar and dual-timezone functionality. Local time shows thanks to the center hands, while you can check your chosen reference time on the center disc. Rolex’s patented everose gold features prominently in this design. The case, oyster bracelet, and fluted bezel are all made from this unique material. Luminous hour markers ensure you can tell the time, even in the dark. This watch is the embodiment of form and function, resulting in a stylish design with practical application.


BUY: $47,995

Sky Dweller White Dial Automatic Men's 18kt Everrose Gold Oyster Watch


13. Day-Date 40 Automatic Silver Dial Men’s 18kt Yellow Gold President Watch

Gold and silver come together in this tasteful Rolex watch. Similar to the other Day-Date designs, the styling is classic and perfect for discerning gents. If you’re selective about how flashy you are, the frosting is minimal, with diamonds on the bezel surrounding the silver dial. You’ll appreciate the 18kt yellow gold president band and case, as well as the ease of checking both the date and the day of the week. It’s water-resistant to 330 feet, so if you get caught in the rain, you’ll be safe in the knowledge it won’t cause any damage. Finally, other details of this luxury watch include the Rolex caliber 3255 automatic movement, secure folding clasp, and luminescent hands and hour markers.


BUY: $41,560

Day Date 40 Automatic Silver Dial Men's 18kt Yellow Gold President Watch


14. GMT-Master II Automatic Men’s 18kt Everose Gold Oyster Coke Bezel Watch

Another soda-inspired watch, this GMT-Master II, takes inspiration from Coke. However, you don’t have to be brand loyal to cola to appreciate this design. The warm tones of the 18kt everose case and three-link oyster bracelet work in harmony with the burgundy and black bezel. Meanwhile, the everose continues on the dial, outlining the hour markers. This makes a nice contrast to the solid black background. You’ll enjoy the practicality of the luminescent hands, oysterlock clasp, and water and scratch resistance, which makes this watch perfect for daily wear. It’s an excellent choice for men who prefer to shift away from tradition and experiment with fun colors in their wardrobe.


BUY: $37,995

Gmt Master Ii Automatic Men's 18kt Everose Gold Oyster Coke Bezel Watch


15. Submariner Date Blue Dial 18K White Gold Oyster Bracelet Automatic Men’s Watch 

There’s no way you’ll be feeling blue with this luxe watch from Rolex. The Submariner is one of the most copied styles and for a good reason. It’s eternally practical, waterproof, and stylish. However, there are no fakes here. The 18kt white gold case and oyster bracelet are the real deal. They’re accompanied by the bright blue of the bezel, as well as the dial. The Mercedes branded sword and Breguet-style hands add to the eliteness and authenticity. It’s the perfect selection of watch for judicious men with a taste for classic with a twist.
BUY: $35,282

Submariner Date Blue Dial 18k White Gold Oyster Bracelet Automatic Men's Watch

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