Might as well get this out of the way now, I am a big fan of Rolex. I used to be a pretty die hard hater...until I got a Pepsi 16710 a few years ago. Since then it has been one of my favorite brands to collect, and the newer models with the updated bracelets are truly everything the brand promises to be. That said, I find the vintage models have a lot of character, history and charm to them. I posed a question recently to the gang on TheRolexForums and asked everyone to list 'Your 5 must have vintage Rolex for under $10k'. I had come up with three I really loved and was curious to see if there were some I didn't even know about that I should consider. Here is the list I walked away with, in no particular order.
#1. Rolex GMT Master 1675 'Radial' Dial - Pepsi bezel
Having had my first Rolex be a nice faded GMT Master II Pepsi dial, and my second be the new Black/Blue GMT Master II, I clearly have a thing for the GMT line. It is a great travel complication, older model bezels can be swapped quickly by yourself for many different looks and they are far less common than the Submariner. What's interesting about this particular vintage GMT is that the dial different from most GMT's you see. If you look closely, you'll notice that the hour lume plots are significantly further away from the minute lines than usual. This is what is referred to as a 'radial' dial. It is a fairly rare variant on the 1675 dial that doesn't seem completely tied to a serial number range. Radial dials can be had at the moment for around $6-8k, a normal GMT from the same time period is more like $5-6k.
#2. Rolex 1680 'Red' Submariner
I have yet to own a Submariner, but if I go vintage it will be hard to resist the temptation of the 'Red' Sub. The matte, maxi-dial (larger luminous plots) with the single, balancing line of red text is starting to rock upwards in value after the rise of its $20k+ price point big brother, the Double Red Sea-Dweller. One of the coolest features of the red submariner is the 'top hat' acrylic crystal dome that sits on top of the case. The watch has so many interesting features and is so well balanced that I feel it has to be on the vintage Rolex short list. While not the rarest, a lot of these have had new dials swapped in by the Rolex Service Centers over the years, so like anything vintage, good condition ones are hard to find. Price is still barely under $10k and climbing fast.
#3. Rolex 5513 'Gilt' Glossy dial
The 5513 is nearly where the Rolex Submariners began. After the 5512 and a few earlier models, rolex stuck with the 5513 for the longest of nearly any other production piece, starting in 1962 and ending in 1990! What's wonderful about some of these early Submariners is the simplicity. For the same reason collectors love the no-date Submariners of today, these had two simple lines of text and no date magnifier as Rolex didn't use those until basically the 1680 (above) came along.
In addition, a 'gilt' dial is one in which the text on the dial is in a golden shade of paint. As you can see on the one above, all the type and the Rolex coronet is all in a golden shade, not in white. The piece pictured is extra special (and maybe slightly out of budget) because it also has a meters first dial on the depth rating. When Rolex was mainly selling in europe, meters was the standard and feet was the secondary unit of measure. After the US market got hot for rolex, they changed all the dials over time to being 'feet first' which are far less rare. On a leather strap these are stunning, simple, purposeful early versions of the most admired watch of all time.
Git versions are just above the $10k mark, whereas white versions start much lower, especially the newer ones, which are just as wonderful but may not appreciate in value as quickly.
#4. Rolex 16758 Gold GMT Master 'Nipple Dial' with Brown Bezel
The nipple dial and all gold case are pure dirty 70s/80s. They styling and nasty brown coloring brings back yuppie businessmen with sideburns and shag carpets. The 'nipple' dial is called that because if you look closely at the hour markers, they appear to be little pyramids with a small nipple of lume. Most hour markers are almost totally covered in lume. The highlights here are the gold case, the brown dial and bezel which is a rare color for Rolex to employ and again, the GMT complication. This wouldn't be my first choice on this list, but would be so much fun to wear on a strap and enjoy on a road trip. Good examples without the gold bracelet are in the $8-10k range.
#5. Rolex 1803 Day-Date with Pie Pan dial
There's a reason the Day Date is called the President. Many of the US Presidents, starting with Eisenhower and moving on to JFK and Reagan (along with countless other world leaders) put this watch on their nightstand before they went to sleep. For around half what most of the watches on this list will cost you, you can pick up an 1803 in solid gold (head only). The 'pie pan' dial is apparent when you look at the edge of the dial where it seems to have a downward slope. If you put the dial face down it looks like a little pie pan! You get not only the kind of history that made Rolex an aspirational brand, but the Day complication which is very cool in real life. While I'm sure you usually know what day it is, letting your Rolex tell you its finally Friday is a true treat. There are lots of different dial variations as the 1803 was made for several decades, and tons exist on ebay for around $4k on a strap or $8k with the solid gold president bracelet.
Note: If you have a gold president bracelet that is saggy, check out my article on Michael Young at Classic Watch Repair who has a magical ability to tighten them again.