The Beckertime Guide to the Best Rolex Watches Under $20,000

As we have been attempting to demonstrate with our mini-series of Rolex price guides, there are watches available from the world’s most famous manufacturer at just about every point along the budget spectrum—particularly when talking about the preowned market.

The factors which affect the value of any model are varied and distinct. Aspects such as age, condition, materials and mechanics all play a part. But two of the most important influences will always be rarity and demand. It is why a humble sports watch cast in stainless steel can sometimes be worth thousands of dollars more than a solid gold dress piece, or an ancient model from the 1950s will go for orders of magnitude more than a brand new one.

Additionally, two examples of ostensibly the same watch that, to the untrained eye, can look very similar might differ in price by extraordinary amounts.

We have already covered what the spans of $5,000 to $10,000 and $10,000 to $15,000 will buy you. We also looked at those ‘money no object’ watches Rolex offers we’re all going to go for once we pick the right six numbers (really enjoyed that one).

For this post, let’s delve into what you can expect to find if you set your parameters to the extremely healthy $15,000 to $20,000 range.

If You Want a Watch to Get You Noticed

The Rolex Day-Date ref. 18238

Rolex’s quintessential Day-Date, alternatively known as the President or the Presidential, is one of those watches, as we mentioned earlier, which can cover a huge bracket of prices with models that look nigh-on identical.

At the lowest end, you can easily obtain specimens of the long-running vintage ref. 1803 for well under $9,000. By comparison, the current equivalent, the ref. 128238, retails for $35,000, and a hyper-rare precursor reference such as the ref. 6511 will set you back about the same as a decent sized house. But stand the three up next to each other and it’s really only watch nerds who are going to be able to tell them apart at first glance.

Where the real differences are is in some of the materials and what lies inside. While all are cast in the finest precious metals (the Day-Date has only ever been issued in solid gold or platinum) it wasn’t until 1979 that the model received its first sapphire crystal dial covering. That was also the year a movement equipped with a Quickset date was introduced, while a double Quickset (allowing for both the day of the week and the date numeral at the three o’clock to be set with the crown) didn’t come along until a decade later.

So, while the styling has been left largely untouched for the best part of 70-years, the Day-Date has become systematically more robust and more convenient as time goes on.

But where does that leave us with our $15k-$20k burning a hole in our pockets? Happily, for that amount of money, we can get the best of both worlds; a reference with all the modern amenities but at a huge discount over a contemporary piece.

The ref. 182XX started life in 1988 and ran all the way up to 2000. It took over from the short-lived ref. 180XX and came with an upgraded caliber, the Cal. 3155, bringing that aforementioned double Quickset.

Available in white gold and platinum (although, curiously, no rose gold) the yellow gold ref. 18238 is the classic look and the one with most plentiful options on the market.

The 36mm model was issued with an exhaustive selection of dials, with and without diamond hour markers. You will find colors ranging from simple blacks and whites, through the traditional champagne, and along to some more extremes like bright reds, oranges and greens. On top of that, this was also the era of wood dials, with some lovely walnut burl faces, and you will come across no shortage of mother of pearl and Jubilee dials too, with the Rolex name monogrammed repeatedly across the face. In short, there is one out there to suit your sensibilities perfectly.

It is difficult to imagine a reference of the Day-Date, the brand’s flagship since 1956, that offers so much for so little. With prices starting at around $18,000 for an example on the eponymous President bracelet, what you are getting is essentially a present-day watch for half price. And it doesn’t get much better than that.

If You Want Something Spectacular

The Rolex Pearlmaster ref. 80319

The Pearlmaster series is one you won’t find in the current line-up. Retired in 2022 following a 30-year run, the collection consisted of a range of ultra-premium jewelry watches modeled on the evergreen Lady-Datejust.

This was Rolex at its most unashamedly luxurious. Every Pearlmaster reference was crafted in one of the three colors of 18k gold and each came with gemstone enhancements of diamonds, rubies or sapphires (sometimes all three) adorning the dial, case or bracelet (and sometimes all three again).

What’s more, it came on its own unique style of bracelet, from which the series took its name. The Pearlmaster bracelet consisted of five links like the Datejust’s Jubilee, but with the proportions reversed. In contrast to the Jubilee’s three small inner links and larger outers, here the inner links are the largest and are flanked by four increasingly smaller ones. All are gently rounded to give a sumptuously comfortable wear as well as being highly distinctive in their own right.

Initially, the collection launched with a 29mm which was three mils bigger than the Lady-Datejust at that time, and a 34mm, the same as the middle of the road Date model. In 2015, the 29mm was quietly withdrawn and a 39mm model was brought in.

In keeping with the Datejust family as a whole, the Pearlmaster was made available in a wide variety of styles. However, unlike the standard range, even the most conservatively tailored Pearlmaster was still created with only one thing in mind; to capture the attention.

The white gold ref. 69329 is arguably the most restrained example, a 29mm beauty with a just single trapezoid-shaped diamond on the bezel at the 12 o’clock. It could even be had with standard Roman or Arabic numerals for hour markers rather than further gems.

At the other end, something like the incredible 39mm ref. 86409RBR, emblazoned with brilliant-cut diamonds literally on every available millimeter, was something even Rick Ross might have had trouble pulling off.

Somewhere between those two extremes was the ref. 80319. One of the original 29mm models, its white gold case was only marginally decorated, confining itself to 12 square-cut diamonds set into the bezel adjacent to each hour marker. It came with a small choice in dials, with black and white the most reserved, while the extremely rare blue sodalite face was something very special indeed.

But perhaps the most successful pairing were those pieces fitted with mother of pearl. The iridescent material taken from the inner lining of various mollusk shells including, appropriately enough, the oyster, has long been favored by Rolex for both its beautiful opalescent sheen and its one-of-a-kind nature—no two dials formed with the mineral are the same.

Today, you will find plenty of examples of the ref. 80319 sitting within our $15k to $20k budget, and they are well worth a look. When in production, the Pearlmaster was a consistently underrepresented collection where advertising was concerned, and so are little known outside of Rolex aficionados. A great way to stand out in more ways than one, what’s life without a little flamboyance?

If You Want One of the Most Important Sports Watches of All Time

The Rolex Daytona ref. 116520

There’s no doubt that Rolex’s only currently existing chronograph, the Daytona, remains one of the most desirable watches in the world. In fact, it has been the object of longing, envy and lust since the second generation emerged in 1988. More recently, the first generation, stemming from the watch’s inception in 1963, an iteration Rolex could barely give away for the first quarter century, have become some of the most expensive and coveted models in vintage watch collecting.

It is a timepiece whose success, or lack thereof, has been inextricably tied to its movement. That misfiring first attempt lingered on shelves due almost entirely to its manually-winding caliber. The automatic engine in the follow-up started it on its stellar trajectory, even though it was produced for them, in its rawest form, by a third party; fellow Swiss compatriots Zenith with their legendary El Primero.

It wasn’t until 2000 and the third generation that the Daytona finally received an in-house movement, the superb Cal. 4130, a caliber that outdid Zenith’s mechanism in just about every respect.

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However, as we said at the beginning, one of the biggest factors driving a watch’s price on the preowned market is its current demand, and for some reason, at this moment, there seems to be more demand for the so-called Zenith Daytonas with their outsourced calibers than for the first of the purely Rolex-powered versions. As a result, the Zenith models are more expensive across the board.

Why that might be is a mystery, but some of it may well come down to collectors with one eye on future returns. The second gen hasn’t quite reached vintage status—yet. It will take another couple of decades for that to happen, but when it does, it’s a pretty safe bet that the value of those pieces is going to go very high indeed. It is, after all, a significant watch, for Rolex and horology as a whole. Canny investors could be getting in early and mothballing these models to cash in down the line.

The good news is that the wonderful and in-house powered ref. 1165XX is presently falling within our price range. And the even better news is that the all-steel ref. 116520 is included in that too.

Any steel Rolex sports watch is massively desirable and none more so than the Daytona. The ref. 116520 is a milestone moment in the life of the model and there has rarely been a better time to secure one for yourself.

With a steel bezel rather than the later Cerachrom-equipped style, it has a more rugged, workmanlike air; a watch that would actually look at home in its originally intended habitat of the racetrack. It also has no equivalent in today’s catalog, the closest in looks currently being the white gold model.

True to those unpretentious roots, the reference was available with only two choices in dial, black or white, both receiving a little pop of color in their bright red Daytona signature curving around the running seconds sub dial at the six o’clock.

What else is there to say about such an historically vital watch? It is one every true Rolex enthusiast should own at some point in their collecting journey, if only for a little while. As with the Zeniths, the time will come when it too is regarded as a vintage icon, and its value will skyrocket.

My advice would be, if you are on the fence, to pull the trigger and pull it soon.