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Rolex has been a household name since its establishment for all the right reasons. The legendary Swiss luxury watch company has an aura that gets better with time. In fact, its crown is among the most recognized symbols globally!
It’s been producing eye-catching timepieces, but it was between the ‘50s and ‘80s when the Crown was enjoying a creative streak. Its timepieces wowed watch enthusiasts with practical complications like the GMT and waterproof cases.
Here are some of the brand’s collection of vintage Rolex watches every collector and enthusiast should own:

Rolex created the first GMT Master timepiece upon request by Pan Am pilots. They needed a watch that would simultaneously keep track of several time zones- home’s and the place they’d be heading to. The GMT Master 1675 1967 model (Pepsi ‘Pink Panther’) served this purpose perfectly.
It has an Oyster case, a matte black dial with white text (matte dials , rounded crown guards, a rotatable aluminum bezel, a Plexiglass crystal, and an Oyster bracelet.

This breathtaking piece with an unconventional moniker is beautiful inside and out. This GMT Master II boasts a thicker-by-5mm stainless steel case, larger crown guards, wider bezel (hence the cringy ‘Fat Lady’), matte black dial with a nice light cream lume, a rotatable black and red bezel, a scratch-resistant sapphire crystal, and an Oyster bracelet.

The Rolex Double Red 1665 got its name from the fact that its dial had two red lines of writing: SEADWELLER, SUBMARINER 2000.
It has a waterproof stainless steel case, a black acrylic bezel, a matte black dial, an acrylic domed (Plexiglass) crystal minus the famous Cyclops date lens, a solid caseback with the word ‘Rolex’ printed horizontally and a matching stainless steel bracelet.

The Rolex Submariner is among the globe’s first purpose-built dive timepieces. The Submariner 5513 was equipped for the job with its stainless steel case, domed acrylic Plexiglass crystal, black maxi dial, pointed crown guards, black aluminum bezel, and a sturdy steel Oyster bracelet.

Rolex produced the Rolex Cosmograph Daytona 6263 (Big Red) for professional speed racing. Its stainless steel case, black dial, black bezel with a tachymeter scale, second-generation screw-down pushers, screw-down caseback, and Oyster bracelet tell it all.

The Rolex Explorer 1016 is a vintage gem that seamlessly combines a sports appearance with a dress wristwatch look. Its durable case is polished and satined and crafted from Rolex’s exclusive stainless steel. It also has a screw-down crown and back, a black dial, a steel bezel, and an Oyster bracelet.

Fondly referred to as the ‘Freccione Era Explorer,’ ‘Steve McQueen Explorer II,’ and ‘The Orange Hand Explorer,’ Rolex created the Rolex Explorer II 1655 with potholers and speleologists in mind. It has a stainless steel case, a steel bezel, a black matte dial, a screw-down caseback, and a matching steel bracelet.

The Rolex Submariner ref. 5512 has a smooth stainless steel case, pointed crown guards, a black dial with minimal clutter, a steel bezel with an aluminum insert, and an Oyster bracelet.

Looking for a simplistic vintage watch that packs an equal punch to that of the classic heavyweights in the Rolex lineup? Look no further than the Rolex Oysterdate 6694.
It’s a nice watch with a minimalist yet eye-catching design with its polished stainless steel casing, clean silver dial, fixed smooth bezel, and smooth Oyster bracelet. It’s among the most affordable vintage Rolex watches. Plus, its smaller size allows it to be equally at home on a lady’s wrist as it would be on a gentleman’s.

The Day-Date President 1803 piece bears the enviable title because countless presidents wore it. It has an elegant Oyster case fashioned from 18K white gold (also available in yellow gold), an 18K white gold caseback, flat acrylic crystal, screw-down crown, 18K white gold bezel, and a luxurious Oyster bracelet.
The table below highlights the main points of our picks above.
|
Model |
Key Features |
Launch Price |
Current Price |
Pre-Owned Price |
|---|---|---|---|---|
|
Rolex GMT-Master Ref. 1675 |
|
S$3,770 |
S$5,931 |
S$18,621 |
|
Rolex GMT-Master (Fat Lady) Ref. 16760 |
|
S$2,590 |
S$3,242 |
S$17,243 |
|
Rolex Sea-Dweller Double Red Ref. 1665 |
|
S$4,110 |
S$4,870 |
S$81,247 |
|
Rolex Submariner Ref. 5513 |
|
S$1,480 |
S$2,717 |
S$23,450 |
|
Rolex Cosmograph Daytona Ref. 6263 |
|
S$110,450 |
S$119,510 |
S$108,628 |
|
Rolex Explorer Ref. 1016 |
|
S$1,310 |
S$4,414 |
S$33,343 |
|
Rolex Explorer II Ref. 1655 |
|
S$2,620 |
S$3,887 |
S$17,945 |
|
Rolex Submariner Ref. 5512 |
|
S$2,875 |
S$3,590 |
S$29,043 |
|
Rolex Oysterdate Precision Ref. 6694 |
|
S$1,460 |
S$2,593 |
S$5,283 |
|
Rolex Day-Date President Ref. 1803 |
|
S$3,840 |
S$5,690 |
S$22,760 |
The Rolex Cosmograph Daytona 6263 is the costliest piece. On the other hand, the Rolex Oysterdate Precision 6694 is the most affordable vintage Rolex.
Although the Rolex 6263’s tachymeter scale and Rolex 1803’s day-date and Stella dial are cool features, our favorite characteristic is Rolex 16760’s advanced movement and bi-colored unidirectional bezel. They allow pilots to keep track of three time zones simultaneously. Check out the full summary below:
It’s probably authentic if it has the appropriate movement, if the serial number on the case and bracelet are similar, if it doesn’t have any typos or fake-looking engravings on the dial or caseback, and if it isn’t oddly heavier than expected. You’re always safer asking an expert to verify it at the end of the day before purchasing.
The Rolex Cosmograph Daytona 6263. It’s one of the most popular sports watches among watch enthusiasts due to its rarity. It’s also linked to the famous American race car driver and actor Paul Newman. The Paul Newman Daytona can earn you lots of profit if it’s in working condition and reasonably good shape.
A Rolex watch is considered a vintage model if it’s been around for at least 30 years. Some timepiece experts raise the bar to a whopping 50 years or more.
A vintage Rolex watch is a timeless classic that’s respected in the watch industry. The right one can complement your look, increase your financial horizon and enable you to enjoy some of Rolex’s best and rarest offerings. Happy watch collecting!
Key Takeaways
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