Rolex, one of the most recognizable luxury brands in the world, crafted a legacy based upon the marriage of two relatively simple yet hugely important technologies: Namely, the Oyster case and the Perpetual automatic movement with 360-degree winding rotor. It was the simple watches that resulted from this marriage—the Oyster Perpetual itself, the Explorer, the Submariner, and others —that cemented the brand’s reputation as a maker of reliable, robust, and highly accurate tool watches.

Nevertheless, Rolex did dip its toes into more complicated watchmaking in the mid-20th century: From chronographs such as the refs. 4113 and 3525 to the triple-calendar moonphase ref. 8171 and Oyster-cased ref. 6062, these creations have become hugely collectible pieces—but no small part of that collectability stems from their rarity, and from the fact that Rolex largely stopped making such complicated fare by the 1950s. But the Swiss marque had a trick up its sleeve—a model simpler than the aforementioned calendar watches that would come to define the brand in the mind of millions of consumers around the world.

In 1956, Rolex debuted the Oyster Perpetual Day-Date, a precious-metal watch with the day of the week displayed in an arc at 12 o’clock; a magnified date window at 3 o’clock; an Oyster waterproof case; and an automatic, chronometer-certified movement. The first automatic, chronometer-certified wristwatch in the world to display the day and date thusly, it was available in several different languages — these would eventually total 26—and was beautifully sized and styled. Soon, its matching “President” bracelet would gain nearly as much fame as the watch itself, lending its name to the entire package and becoming synonymous in the minds of many with opulence and wealth.

The “President” nickname was an apt one: The Day-Date was quickly seen on the wrists of American presidents such as Lyndon B. Johnson, Richard Nixon, Gerald Ford, and Donald Trump. Athletes such as Jack Nicklaus and LeBron James; actors such as Jacob Elordi and Jennifer Aniston; musicians such as John Mayer and Bono—all across the world, celebrities have adopted this gold or platinum timepiece as their own. As the only Rolex model solely available in precious metals, it has a unique place in the Crown’s catalog as a signifier of wealth and status, and is often used as a prop or a trope in television and films for this reason. (For a fun evening, count the number of Day-Dates seen in any given episode of The Sopranos.)

Over the years, a dizzying array of special dials and configurations have been seen on this sparkling model: From burled wood to precious stones to the beautiful colored “Stella” references of the 1970s and 1980s, these Day-Dates are incredibly varied and nuanced, resulting in a veritable collector’s paradise of compelling options. Beginning around $8,000-$10,000 for a vintage four-digit reference on a strap and continuing into “If You Have to Ask” territory for special off-catalog or double-signed references, the Day-Date is most certainly not beginner’s horological fare . . . but if bought correctly, it could very well constitute a one-watch collection.

How to Use This Guide
While attempting to catalog every possible Day-Date configuration from the past 70 years would be a fool’s errand, examining significant references from each generation is eminently doable. Below you’ll find an example reference of each along with a pricing reference for that generation and specifics about its aesthetic and technical considerations. Keep in mind that the earliest generations are fairly rare and accurate pricing information is thus tougher to pin down. Four- and five-digit watches, however, are much more abundant and can be had from knowledgeable dealers. Rolex’s CPO program also forms a convenient entry point into collecting the Day-Date.