Shopping Time: The 5 Most Outrageous Rolex Day-Dates You Can Buy Right Now

We are always scouring the web for the most amazing watches currently available, and each Friday Shopping Time shares five standout timepieces with you.

Prices on Rolex sports watches are dropping, but not for the suddenly popular Day-Date 36. Last week, we reported in detail about why the Rolex Day-Date has shot up in value—a full 57 percent, according to watch market index Everywatch. You know we love our watch market data, so much so that we have a primer on how to use watch market data to inform your collecting. And while hearing about dropping prices on everything from the the Rolex GMT Master, to the Submariner, to a bevy of good deals on current Rolex references, and, yes, even the modern Daytona is always good news, it’s also pretty fascinating when a watch shoots up in value—especially if you own one—but also because it indicates a shift in trends.

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We waxed poetic about the rise of the small watch, and even the possible influence of coastal-elite tastes in bringing back the Day-Date with a vengeance, but it’s also been on the wrists of some serious global influencers in the past year or so, including Jay-Z, LeBron James, David Beckham, Idris Elba, and John Mayer.

Winston Churchill, Dwight Eisenhower, Lyndon B. Johnson, Richard Nixon, Gerald Ford, Ronald Regan, and Donald Trump have all worn the Day-Date while in office, and so the watch is now broadly known as the President—as is its special bracelet that is (almost never) offered on other models. Until the Rolex Sky-Dweller came out in 2012, the Day-Date had remained the most complicated watch in the Crown’s catalog, with its day of the week and date complications displayed broadly on the outside of the dial. At the time of its release in 1956, the Day-Date was the first watch to include a week-day complication with the full name of the day spelled out, and it remains an iconic reminder of how wildly innovative Rolex founder Hans Wilsdorf was before he passed away in 1960.

While we are happy that Rolex is acting like Rolex again, making relatively conservative watches, it is not without some pleasure that we take in the most outrageous Day-Dates currently on the market. With prices up a full 57 percent in August alone, why not swim with the current and see what the most expensive and rare Day-Dates are looking like?

Below are the five most outrageous and amazing Day-Dates currently on the market.

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Rolex Day-Date ref. 18238 with Coral Dial | $165,000

Rolex Day-Date ref. 18238 with Coral Dial | $165,000
Rolex Day-Date ref. 18238 with Coral Dial | $165,000

One thing we love about the Day-Date is just how diverse and surprising it can be. The sheer breadth of variety and creativity expressed in different dial executions is matched only by the watch’s ability to seemingly look good in every one of them. As stone dials and big colors continue to make a resurgence, references such as this 18238 from the early ‘90s are once again being celebrated for their unique beauty. Few are more unique than what we see here in the iconic Day-Date.

This example features a scarcely produced factory stone Coral dial, and it is absolutely stunning. The soft palate expressed in this stone is left unhindered by hour markers and scales, leaving just the defining day and date complications. The stone is set within a 36 mm yellow gold case in excellent, near new condition. The caseback even retains its sticker. The dial itself is the star of the show here, and it appears to be free of cracks. This watch is being offered by The Keystone, and comes as a full kit example. This is a rare opportunity to own a watch seldom seen in the market, and represents one of the most unique Day-Date references ever made.

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Rolex Day-Date ref. 1804 ‘Stella’ | €100,000 (~$112,000)

Rolex Day-Date ref. 1804 ‘Stella’ | €100,000 (~$112,000)
Rolex Day-Date ref. 1804 ‘Stella’ | €100,000 (~$112,000)

In the 1970s, Rolex saw fit to adorn their most complicated watch (at the time) with bold, colorful lacquer dials. The bright colored dials are collectively known as ‘Stella’ dials, after the Swiss based company that produced the dials for Rolex. These dials are prized by collectors and enthusiasts today for their expressive personalities, relative rarity, and the unique shades they can take due to the manner in which they were made. Oh, and in typical Rolex fashion, there were more colors produced than were officially listed in the catalog. Not only is there an inherent mysterial element to these watches, there is also something larger than life about these colors in the context of the precious metal cases of the Day-Date. It was a bid for a younger audience, however, and it kind of flopped because the Day-Date just wasn’t a youthful model, nor within financial reach of the young. So, not that many sold, and thus not that many were made.

This example on offer from Amsterdam Vintage Watches features a stunning bright turquoise dial, which has been gem-set at the hour markers and around the bezel. This dial is set within a 36 mm white gold case, pushing all focus to the brilliant diamond-set dial. Even if you’re not one for diamonds, it’s difficult to deny the captivating effect they have here. This example was produced in 1978, and while it shows signs of wear given its age, it remains in excellent condition overall. This is one of the most captivating examples of the Stella-dial Day-Dates, and looks as brilliant today as it did in the ‘70s.

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Rolex Day-Date ref. 1803 ‘Rose Guilloche’ | €98,000 (~$110,000)

Rolex Day-Date ref. 1803 ‘Rose Guilloche’ | €98,000 (~$110,000)
Rolex Day-Date ref. 1803 ‘Rose Guilloche’ | €98,000 (~$110,000)

Before they did big colors, Rolex showed an interest in subtle, unique dial textures within their Day-Date collection, and this reference 1803 is one of the most interesting examples. This dial rewards a closer look, with a rich texture that sets a block motif within the guilloche pattern. The warm gray tone offers another layer of personality, pairing perfectly with the rose gold case. As incredible as the dial is, one other unusual feature here is the application of a riveted Oyster bracelet, rather than the typical President bracelet. This watch is a very rare sight rendered in rose gold in this era. Its use here pushes the focal point to the subtle dial texture rather than compete with it.

This specific example again comes to use from Amsterdam Vintage Watches, and is remarkably preserved. It’s clear that this was a special watch from day-one, and while it does show signs of age, it shows very little in the way or wear and tear. The French day aperture brings a fitting final touch to this incredibly distinctive Day-Date. I absolutely love this dial and if you prefer to fly under the radar, this could be the end-game Day-Date for you.

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Rolex Day-Date ref. 18238 ‘Blood Moon’ | $42,850

Rolex Day-Date ref. 18238 ‘Blood Moon’ | $42,850
Rolex Day-Date ref. 18238 ‘Blood Moon’ | $42,850

A full pavé diamond set dial may sound a bit ostentatious, but this reference 18238 manages to capture a demure vibe thanks to the way it’s been executed. This dial features deep red ruby hour makers that sink into the sparkling landscape surrounding them. What we love about this dial is that the proportions of those ruby hour-markers are maintained (unlike the more typical square diamond hour-markers) and the settings are all tucked up neatly to create a single, harmonious balance in the shapes as well as in the colors.

This is a configuration that would be considered “off-catalog” these days, with this example, offered by Tropical Watch, hailing from 1994. In other words, this is a rare bird. This watch is being offered as a full set with box and papers, and features a case and bracelet in exceptional condition with only light signs of wear. There’s something quite captivating in this dial, and it’s been done in a way that should appeal to even those who prefer no gems in sight.

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Rolex Day-Date ref. 18038 ‘Stella’ | CHF62,000 (~$73,000)

Rolex Day-Date ref. 18038 ‘Stella’ | CHF62,000 (~$73,000)
Rolex Day-Date ref. 18038 ‘Stella’ | CHF62,000 (~$73,000)

Finally, we have another Day-Date “Stella,” this time with a brilliant green lacquer dial. There were four distinct variations of the Stella dial, with this one being a series three as noted by the flat dial and “T Swiss Made T” marking along the bottom. Due to the pigments being mixed by hand, the colors of these dials do have a range of variations, and this tone of green perfectly compliments the yellow-gold case. It’s an undeniably great combination, and one that Rolex still riffs on to this day within the Day-Date collection. No modern green-dial Day-Date is quite as vibrant as we see here, however.

This reference 18038 with green Stella dial is available from Roy & Sacha Davidoff, and has aged in a beautifully subtle manner. The dial itself is free of any cracks or damage, representing a well preserved example of a rare dial. All of the lume plots are intact, and have aged to a pleasing off-white color. The 36 mm yellow-gold case shows very little signs of wear, making this something of a time capsule of an important era—not only of the Day-Date, but of Rolex itself as it transitioned into the modern era.

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Please note that we are not affiliated with the sellers of the watches we recommend. We may point out aspects of a listing that we feel are positive, but only you can vet a seller. We can recommend viewing our video “How to Collect It: Vintage Watches” to glean some best practices, however.