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Rolex watches
Rolex watches are sought after for its quality and trademark style. Pixabay

Out of all the vintage luxury watch brands out there, Rolex has to be the most recognizable. Its name rings across multiple generations. Because of this, it has become one of the most sought after brands among watch collectors.

Watch collectors tend to grow an obsession over Rolex watches because of the brand’s intrinsic value that also grows over time. Aside from being fascinatingly purpose-built and durable, the details and intricacies on Rolex watches have also captivated the hearts of anyone who’s seen or used one.

Here are 40 of the best vintage Rolex watches for men that you can still cop for yourself.

1. Rolex Vintage President 1807 Bark Finish

Rolex Vintage President 1807 Bark Finish
Rolex Vintage President 1807 Bark Finish Bob's Watches

Equipped with an 18 karat yellow gold 36mm Oyster case, the vintage President Day-Date will look and feel impressive on the wrist. The day and date displays at the 12- and 3-hour markers make this instantly recognizable as a Rolex Day-Date, the go-to watch for several American Presidents and world leaders.

2. Vintage 1952 Rolex Oyster Perpetual 6107

Vintage 1952 Rolex Oyster Perpetual 6107
Vintage 1952 Rolex Oyster Perpetual 6107 Bob's Watches

This watch screams classic and vintage. It has an original dial that has aged to a rich tropical patina and displays the time via older-style gold dagger hour markers and sword hands. Mass interest for vintage timepieces such as this is at an all-time high so it is definitely an opportune time to get one for yourself. A Rolex Oyster Perpetual is essential for any luxury watch collection

3. Rolex DateJust Stainless Steel Vintage 1603

Rolex DateJust Stainless Steel Vintage 1603
Rolex DateJust Stainless Steel Vintage 1603 Bob's Watches

The Datejust reference 1603 has an all-steel design with a 36mm stainless steel Oyster case, engine-turned bezel, Oyster bracelet, and Fliplock clasp that all coalesce to render its sleek aesthetic. It is built to be resilient and versatile thus being an appropriate watch for any occasion or adventure.

4. Vintage Rolex 4919

Vintage Rolex 4919
Vintage Rolex 4919 Bob's Watches

Desired by many Rolex enthusiasts, the 4919 Bubbleback exudes vintage charm with its older-style bubble back case, thicker acrylic crystal and ivory dial adorned with bamboo leaf hands. Measuring 31mm in diameter, this edition suits a broad range of wrist sizes and will easily become the most interesting vintage Rolex in your collection.

5. Rolex Datejust 1601 Vintage

Rolex Datejust 1601 Vintage
Rolex Datejust 1601 Vintage Bob's Watches

This edition of the steel and gold Oyster Perpetual Datejust gives you a sophisticated look. It sports a stunning champagne Pie Pan dial and an older-style Oyster case with tapered lugs. The particular unit is in excellent condition for a vintage wristwatch.

6. Rolex Vintage President 1803

Rolex Vintage President 1803
Rolex Vintage President 1803 Bob's Watches

Belonging to the prestigious Day-Date collection, this vintage Rolex Presidential Day-Date ref. 1803 features an exquisite 18-karat yellow gold finish with polished and satin elements nicely paired with a timeless and very desirable champagne dial. This is your chance to add an iconic vintage Tiffany & Co Rolex to your collection.

7. Vintage 1972 Rolex 1680 Red Submariner

Vintage 1972 Rolex 1680 Red Submariner
Vintage 1972 Rolex 1680 Red Submariner Bob's Watches

The vintage Submariner 1680 features a stainless steel 12-link Oyster Rivet bracelet and a matte black tritium “Red Submariner” dial topped with sandy hour markers and matching hands framed by an excellent lightly faded black bezel insert. This model is accurate to the second, very comfortable, and comes with a beautiful patina.

8. Vintage 1963 Rolex Datejust 6305 Silver Dial

Vintage 1963 Rolex Datejust 6305 Silver Dial
Vintage 1963 Rolex Datejust 6305 Silver Dial Bob's Watches

In excellent condition for a watch of its age, this preowned older-model Datejust boasts a sophisticated feature set which includes a silver “pie pan” dial topped with dagger hour markers, sword-shaped hands, and aged Tritium luminous plots framed by a fluted bezel in yellow gold. This stunning timepiece can be yours for a very competitive price.

9. Vintage Rolex Day-Date 1803 ‘Pie Pan’ Dial Leather Strap

Vintage Rolex Day Date 1803 'Pie Pan' Dial Leather Strap
Vintage Rolex Day Date 1803 'Pie Pan' Dial Leather Strap Bob's Watches

A true and ageless icon that will never go out of style, the President’s Watch continues to top must-have lists of collectors. With a feature set including a classic 36mm Oyster case in impeccable yellow gold and an amazing “pie pan” dial with elegant hands and tritium plots, the ref. 1803 will surely hold its value.

10. Vintage Rolex Date 1502 Florentine Finish

Vintage Rolex Date 1502 Florentine Finish
Vintage Rolex Date 1502 Florentine Finish Bob's Watches

Belonging to the first collection of Rolex movements produced entirely in-house, the ref. 1502 is an intriguing collector’s item. Showcasing an 18 karat yellow gold finish and a 34mm Oyster case containing a calibre 1560 Perpetual movement which offers a reliable reading via 18,000 bph, the Date ref. 1502 undeniably brings immense character to any watch box.

11. Vintage Rolex 5500 Air-King

11 Vintage Rolex 5500 Air-King
11 Vintage Rolex 5500 Air-King Bob's Watches

This successful edition of the Air-King collection, now readily available on the used Rolex market, will appeal to those looking for an affordable and versatile entry-level vintage timepiece. Boasting a stainless steel finish, flat-link Oyster bracelet, and a comfortable 34mm case housing a cal. 1520 self-winding movement, the Air-King can be your sophisticated weekender or your daily watch.

12. Vintage Rolex Oyster Perpetual 6634

12 Vintage Rolex Oyster Perpetual 6634
12 Vintage Rolex Oyster Perpetual 6634 Bob's Watches

In 1931, five years after Rolex patented their Oyster case thus offering the first fully waterproof watch, they patented the pioneering Perpetual movement. Eventually, a timeless icon, the Oyster Perpetual, was born. Showcasing a yellow gold finish and a white dial adorned with yellow gold indices and sweeping hands, this vintage Rolex 6634 truly exudes class.

13. Vintage Rolex Explorer 1016 Arabic Markers

13 Vintage Rolex Explorer 1016 Arabic Markers
13 Vintage Rolex Explorer 1016 Arabic Markers Bob's Watches

With a stainless steel case housing an automatic 1570 movement and an amazing matte black dial topped with light creamy Arabic hour markers and lumed hands, all secured by an excellent 78360 bracelet, the Explorer 1016 will appeal to those seeking a gorgeous timepiece with history and a classy look and feel.

14. Vintage Rolex Sea-Dweller 1665 Rail Dial 1979

14 Vintage Rolex Sea-Dweller 1665 Rail Dial 1979
14 Vintage Rolex Sea-Dweller 1665 Rail Dial 1979 Bob's Watches

Launched in 1967, the Sea-Dweller line was designed for deep-sea exploration and engineered to be waterproof to a depth of 1,220 meters. This vintage Rolex Sea-Dweller 1665 features a 12-link 93150 bracelet and a slightly faded but excellent black bezel insert framing a unique matte black “rail” dial with creamy yellow hour markers.

15. Vintage Rolex Oyster Perpetual 6564

15 Vintage 6564 Rolex
15 Vintage 6564 Rolex Bob's Watches

Introduced in the 1950s, this timeless dress watch has since become a widely sought-after collector’s item for its attractive entry-level price point and modest styling. This stunning vintage edition boasts an older-style rivet link bracelet and an aged dial with dagger hour markers, long tapered dauphine hands in yellow gold, and a very desirable patina.

16. Vintage Rolex GMT-Master 1675 Black Nipple Dial

16 129072 Vintage Rolex GMT-Master 1675 Black Nipple Dial
16 129072 Vintage Rolex GMT-Master 1675 Black Nipple Dial Bob's Watches

The Rolex GMT-Master was designed to show two time zones simultaneously. This vintage model features a two-tone case, a stainless steel and 14-karat yellow gold fold-over link Jubilee bracelet, and a glossy gilt black version of the rare “nipple dial” topped with luminous markers and hands. This is a classy timepiece for professionals criss-crossing the globe.

17. Vintage Rolex Submariner Watch 5513

Diver watches for unser $100
These diver watches are a great deal for under $100 Bob's Watches

Launched in 1953, the Submariner line set the standard for dive watches by showcasing the first timepieces waterproof to a depth of 100 meters. This vintage Submariner features a stainless steel 12-link Oyster Rivet bracelet and a “meters first” dial adorned with light creamy yellow markers and hands and framed by an excellent faded “long 5” black bezel insert.

18. Rolex Vintage GMT-Master 1675

18 Rolex Vintage GMT-Master 1675 Root Beer
18 Rolex Vintage GMT-Master 1675 Root Beer Bob's Watches

Another GMT-Master, this model showcases the rare nipple dial, in an excellent brown “Root Beer” hue, topped with warm sandy markers and hands framed by a matching bezel insert that has faded beautifully and is in excellent condition. This handsome tool watch suits both the globetrotter and the everyman.

19. 1979 Vintage Rolex Submariner 1680

19 1979 Vintage Rolex Submariner 1680
19 1979 Vintage Rolex Submariner 1680 Bob's Watches

This vintage Submariner features an excellent case with its original factory bevels still intact. Its black bezel insert, which has faded to a stunning navy blue color, surrounds a matte black tritium pumpkin dial topped with warm yellow orange hour markers and matching hands.

20. Vintage 1970 Rolex GMT-Master 1675 Root Beer

20 Rolex Vintage GMT-Master 1675 Root Beer
20 Rolex Vintage GMT-Master 1675 Root Beer Bob's Watches

This vintage GMT-Master’s feature set includes an acrylic crystal, waterproof screw-down crown, and an 18-karat yellow gold case, paired with an evenly faded Root Beer bezel framing a service brown nipple dial with matching hands and an automatic 1570 movement. A stylish addition to your collection.

21. Vintage Rolex GMT-Master 1675 Pepsi Circa 1972

21 Vintage Rolex GMT-Master 1675 'Pepsi' Circa 1972 cropped
21 Vintage Rolex GMT-Master 1675 'Pepsi' Circa 1972 cropped Bob's Watches

Nicknamed the “Pepsi” for its characteristic blue and red bezel, this sought-after timepiece’s feature set showcases an excellent case, an acrylic crystal over a matte black tritium dial adorned with creamy markers and hands, and an excellent 78360 12-link bracelet.

22. Vintage 1967 Rolex Milgauss 1019 CERN dial

22 Vintage 1967 Rolex Milgauss 1019 CERN Dial
22 Vintage 1967 Rolex Milgauss 1019 CERN Dial Bob's Watches

The Milgauss line is the only Rolex offering clad with tinted crystal. This particular one has an excellent case with its serial number still crisp and well-defined. The Milgauss is one of the timeless classics from the entire Rolex collection and most watch collectors deem it a good investment.

23. Men's Vintage Rolex Air-King 5500

23 Men's Vintage Rolex Air-King 5500
23 Men's Vintage Rolex Air-King 5500 Bob's Watches

Adored by many collectors since day one for its simple yet sophisticated style, the Air-King boasts a stainless steel 34mm case, Oyster bracelet secured by a Fliplock clasp, and an elegant dial with slim index hour markers, dauphine hands, and the Rolex coronet at the 12 position. The Air-King is a versatile statement piece with a modest design and price.

24. Vintage 1980 Rolex Submariner 1680 Feet First Dial

24 Vintage 1980 Rolex Submariner 1680 Feet First Dial
24 Vintage 1980 Rolex Submariner 1680 Feet First Dial Bob's Watches

The Vintage 1980 Rolex Submariner 1680 catches the eyes of any savvy watch enthusiast with its automatic 1570 movement with date, waterproof screw-down crown, unidirectional rotatable time-lapse diver's bezel, and acrylic crystal. This particular watch is sold at an affordable price while still having its original factory bevels intact.

25. Vintage Rolex Men’s GMT-Master 1675 Black Nipple Dial

25 Vintage Rolex Mens GMT-Master 1675 Black 'Nipple' Dial
25 Vintage Rolex Mens GMT-Master 1675 Black 'Nipple' Dial Bob's Watches

This stylish Vintage Rolex Men’s GMT-Master 1675 sports a black bezel insert that exudes grandeur. It has a stunning glossy black tritium nipple dial with light creamy patina and matching hands.

26. Rolex Day-Date 1802 German Day

26 Pre-Owned Rolex Day-Date 1802 German Day
26 Pre-Owned Rolex Day-Date 1802 German Day Bob's Watches

This stunning dress watch has the date located at the 3-hour marker, thus the series name Day-Date. It is highly regarded because of the exquisite styling of the cases and bracelet clad in stunning 18 karat yellow gold finish. This vintage edition also features an acrylic crystal over the dial.

27. Vintage 1982 Rolex Submariner 16800 Matte Tritium Dial

27 Vintage 1982 Rolex Submariner 16800 Matte Tritium Dial
27 Vintage 1982 Rolex Submariner 16800 Matte Tritium Dial Bob's Watches

The first reference in the Submariner line to have a depth rating of 300 meters, the transitional Rolex 16800 was also the first to utilize a scratch-resistant sapphire crystal and the impressive calibre 3035 Perpetual movement. This example features a classic 40mm Oyster case, unidirectional bezel, and flat-link Oyster bracelet to make a very desirable collector’s item.

28. Rolex 1002 Oyster Perpetual

28 Pre Owned Rolex 1002 Oyster Perpetual
28 Pre Owned Rolex 1002 Oyster Perpetual Bob's Watches

One of the most sought-after Oyster Perpetual references among collectors is the 1002, here presented with its classic stainless steel 34mm case surrounded by a smooth bezel framing a striking blue Shantung dial topped with tritium lume and long, tapered hands. This timepiece is an attractive choice for anyone seeking an iconic vintage Rolex at an entry-level price.

29. Rolex Speedking 6020

29 Rolex Speedking 6020
29 Rolex Speedking 6020 Bob's Watches

The Speedking 6020 features a 31mm yellow gold case housing a manual-winding movement and older-style dagger hour markers and dauphine hands on the dial topped with tritium lume that has aged to a warm patina which complements the case’s gold hue. Add this rare and attention-grabbing collector’s item to your collection for an affordable price.

30. Rolex Oyster 6426 Black Dial

30 Pre-Owned Rolex Oyster 6426 Black Dial
30 Pre-Owned Rolex Oyster 6426 Black Dial Bob's Watches

Outfitted with an intriguing hand-wound movement, this stunning edition of the iconic vintage Oyster Precision is presented in stainless steel with an elegant leather bracelet and sharp black dial adorned with silver indices and hands. For an affordable price, you can get this bold yet sophisticated timepiece that exudes a level of class and elegance many collectors seek.

31. Vintage Rolex Submariner 5513 Black Maxi Dial

31 Vintage Rolex Submariner 5513 Black Maxi Dial
31 Vintage Rolex Submariner 5513 Black Maxi Dial Bob's Watches

The Submariner series is a timeless classic. The 5513 was launched in the early ‘60s and made until the late ‘80s, having the longest production run of all Submariner models. What’s most sought after in this watch is it bears all the classic aesthetics of the original from its maxi dial to its larger lume plots and consistent light and creamy patina.

32. Vintage Submariner Rolex 5513

32 Vintage Submariner Rolex 5513
32 Vintage Submariner Rolex 5513 Bob's Watches

This particular watch bears all the classic characteristics of the timeless Vintage Rolex Submariner 5513 and is in excellent condition. It features a pristine dial with an incredibly well-aged, ghost, "kissing 4" dial. It is one of the more commonly seen Rolex timepieces but still makes for a stunning and sophisticated piece.

33. Vintage Rolex Steel Oyster Precision 6423

33 Vintage Rolex Steel Oyster Precision 6423
33 Vintage Rolex Steel Oyster Precision 6423 Bob's Watches

Running on an intricate hand-wound movement, the reliable OysterDate Precision ref. 6423 features a stunning silver dial topped with older-style indices, Arrowhead hands, and plots that have aged to an amazing patina. With a size and weight that will flatter most wrist sizes, this model will appeal to those seeking a watch with incredible character and history.

34. Rolex Date 15010 Steel Oyster

34 Pre-Owned Rolex Date 15010 Steel Oyster
34 Pre-Owned Rolex Date 15010 Steel Oyster Bob's Watches

Sought-after by first-time collectors for its attractive price tag, this variation of the remarkably versatile Oyster Perpetual Date features a contrasting dial and engine-turned bezel crafted from some of the world’s finest materials. Outfitted with a reliable Perpetual movement safely housed within the tough waterproof Oyster case, the 15010 is for anyone who seeks to make a powerful impression.

35. Vintage 1967 Rolex Submariner 5513

35 Vintage 1967 Rolex Submariner 5513
35 Vintage 1967 Rolex Submariner 5513 Bob's Watches

The Rolex Submariner is one of the more versatile series by the brand. While all of them have their own particular appeal to collectors, the 5513 is considered an essential part of a collection. This 5513 was made in 1967 which places it fairly early in that production run. This watch has all the components in excellent condition and will surely be a worthy addition to your collection.

36. Rolex Oyster Perpetual 1007 Stainless Steel

36 Rolex Oyster Perpetual 1007 Stainless Steel
36 Rolex Oyster Perpetual 1007 Stainless Steel Bob's Watches

An all-steel edition of the vintage Oyster Perpetual, the 1007 exudes retro elegance with its matching silver dial adorned with tapered dauphine hands and lumed plots filled with creamy tritium. With a desirable 34mm case size sought after for its tough exterior and unassuming size and weight, this edition is irresistible.

37. Unpolished Rolex King Midas 3580

37 Pre-Owned Unpolished Rolex King Midas 3580
37 Pre-Owned Unpolished Rolex King Midas 3580 Bob's Watches

With its retro asymmetrical case and integrated bracelet, the all-gold King Midas is unlike anything else in the brand’s collection. Running on an intricate hand-wound movement and featuring a matching champagne dial, this model of the King Midas 3580 also comes with the original urn box all for a competitive price.

38. Vintage Rolex GMT-Master 6542 Bakelite Bezel Nipple Dial

38 Vintage Rolex GMT-Master 6542 Bakelite Bezel Nipple Dial
38 Vintage Rolex GMT-Master 6542 Bakelite Bezel Nipple Dial Bob's Watches

This vintage GMT-Master boasts an excellent original case with a glossy chapter ring dial with nipple markers and matching dauphine hands framed by a very desirable Root Beer Bakelite bezel insert. This reference is secured by a stylish tan Italian leather strap with gold Rolex tang buckle.

39. Rolex Black Dial Submariner 16610

39 Used Rolex Black Dial Submariner 16610
39 Used Rolex Black Dial Submariner 16610 Bob's Watches

A popular choice among collectors, this example of the ref. 16610 notably features holes in the lugs and older-style tritium lume on the dial. With a depth rating of up to 1,000 feet and running on a Perpetual movement with self-winding, this all-steel Submariner is a versatile and reliable timepiece.

40. Rolex Datejust 16013 Champagne Jubilee Dial

40 Men's Rolex Datejust 16013 Champagne Jubilee Dial
40 Men's Rolex Datejust 16013 Champagne Jubilee Dial Bob's Watches

Since its introduction in 1945, the Datejust has graced the wrists of influential men all over the world. Instantly recognizable for its fluted bezel, Jubilee bracelet, automatically changing date aperture, and steel and yellow gold waterproof Oyster case, the ref. 16013 is suitable for both casual and formal occasions and has become the go-to dress watch for many.