Keeping Calendar: A New Perspective on a Classic Complication

Any watch can tell you the time of day, but the upper echelons of watchmaking offer much more than just hours and minutes. They also display the day, the date, the month — even the phases of the moon. And, while having this information on your wrist can often be useful, the tricky task of displaying these figures accurately (taking into account the varying length of each month, as well as leap years) is a daunting horological feat. But that makes this selection of striking, sophisticated timepieces worth their place in your collection — any day of the week.

Rolex Sky-Dweller

Rolex Sky-Dweller
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Featuring one of Rolex’s most complicated movements, this travel-friendly timepiece indicates local time on its hands and a second (home) time on the ingenious 24-hour dial at the centre. Better still for frequent flyers, the Saros annual calendar displays the day and month, and will automatically differentiate between 30 and 31-day months. ($18,450)

Frederique Constant Classics Quartz Chronograph Triple Calendar

Frederique Constant Classics Quartz Chronograph Triple Calendar
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Despite being powered by a battery and not a mechanical rotor, Frederique Constant’s classic triple-calendar delivers top-shelf modern design, with a day and month display at 12, a punchy red-tipped pointer displaying the date, and a chronograph for good measure. ($1,695)

Vacheron Constantin Traditionelle Complete Calendar

Vacheron Constantin Traditionelle Complete Calendar
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Calendars have been a feature of high-end watches since the 1700s and this complete calendar (which is similar to an annual calendar) has all of the sophistication of those classical forebears in a sleek office-ready case that’s just 10.72 mm thick. ($61,000)

IWC Portofino Perpetual Calendar

IWC Portofino Perpetual Calendar
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There’s a good reason that perpetual calendars like this demand such a premium over annual calendars. An annual calendar needs to be adjusted each year on the first of March, but (assuming your watch stays wound and running) a perpetual calendar like this won’t require adjustment until the year 2100. Not bad for a bunch of tiny gears. ($32,400)

Citizen Calendrier

Citizen Calendrier
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Calendar watches are complicated, but that doesn’t mean they have to cost a fortune. This Eco-Drive powered Citizen, which will run indefinitely on any kind of light, punches far above its price with an annual calendar and a 24-zone world time function. ($525)

Omega Constellation Globemaster Co-axial Master Chronometer Annual Calendar

Omega Constellation Globemaster Co-axial Master Chronometer Annual Calendar
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The Globemaster’s “pie-pan” dial is a nod to one of the first Constellation models from the 1950s. But Omega’s Co-Axial Master Chronometer Annual Calendar Calibre 8922 movement is fully modern, with a dedicated hand indicating the months of the year in each of the dial’s 12 facets. ($12,600)

Breitling Premier B25 Datora 42

Breitling Premier B25 Datora 42
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Willy Breitling called the Premier line an “unmistakable stamp of impeccable taste” when he launched it in the 1950s, and it has lost none of its appeal in the decades since. From its rectangular pushers to its salmon-hued dial with day, date, month, and moon-phase displays, this is as highbrow as chronographs come. ($17,550)

Seiko Presage Craftsmanship Series SPB393

Seiko Presage Craftsmanship Series SPB393
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A distinctive dial layout combines Roman numerals with a retrograde day and date display (one that completes an arc before snapping back to its first position) as well as a power reserve indicator. More superior still is the dial itself, which is expertly enamelled for a welcoming warmth of colour. ($2,195)

Glashütte Original PanoMaticCalendar

Glashütte Original PanoMaticCalendar
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There are many variations of the annual calendar, but few are as distinctive as the PanoMaticCalendar. Its unique dial layout includes a large subdial for hours, another subdial for seconds, a retrograde month display, and a moon phase. Plus, with an impressive 100 hours of power reserve, it’ll keep ticking for more than four full days between wears. ($35,500)

Tudor Royal

Tudor Royal
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Day-date watches such as this one have been a go-to for presidents, CEOs, and other stylish high-flyers since the 1950s. The combination of a classic day-date layout with a deep blue Roman numeral dial and a 1970s-style integrated bracelet lends the Royal even more gravitas. ($3,060)

Photography: Michael Kazimierczuk (Impossible Studios)

Prop Styling: Tricia Hall (Plutino Group)

Styling: Haley Dach

Photo Assistant: Ethan Allen

Text: Jeremy Freed