The best men’s watches for $20,000 are the star of tonight’s show, and no star shines brighter than the 2021 Rolex Sky Dweller. Since its shock 2012 Baselworld debut, the Rolex Sky Dweller has been the most versatile watch in the catalog. Tonight, Tim Mosso reviews the Sky Dweller alongside six outstanding luxury watches priced at or below twenty thousand dollars. This is a watch collector’s guide to finding excellent value at a clear cut premium luxury price point.

For 2021, Rolex has made small changes to the Sky Dweller lineup, but the most consequential is the arrival of a new Rolex Jubilee bracelet. For an extra $250 in stainless steel, a Rolex collector can complement his S-D with the same supple five-link dress band used on Rolex Datejust models since 1945. Rolex collectors have remarked for years that the Sky Dweller resembles a 42mm Datejust, so the pairing of SD and Jubilee is a natural evolution.

Looking back nine years, it’s clear that the Rolex annual calendar GMT got off to a challenging start.

Baselworld 2012 brought a shock for Rolex buyers. The Oyster Perpetual Sky Dweller, a GMT with an annual calendar, marked a new era of complicated Rolex watchmaking. Literally no one had forecast this model’s arrival, and that in spite of Rolex spending years prior filing multiple patents for annual calendar mechanisms. But in its initial all-gold form, the Sky Dweller wasn’t a best seller. The price was too high, the dial lacked lume by sports watch standards, and on a full precious metal bracelet, the 42mm watch was a ponderous thing.

All of that changed at Baselworld 2017. That year, Rolex introduced a new Sky Dweller model, the reference 326934. The major innovation was its majority stainless steel construction; only the fluted Ring Command bezel remained in white gold. Moreover, the availability of more attractive dials, greater luminescence at night, and – far – more attractive price points led to the Sky Dweller’s first mainstream swell of demand at Rolex dealers. Suddenly, watch collectors who would have bought GMT Master IIs, Daytonas, and Submariners were players for the Sky Dweller.

The 2017 changes helped to bring out the sheer capability of the Sky Dweller platform. What had seemed underwhelming at prices over $40,000 became an excellent mix of virtues at under $15,000. Each “steel” Sky Dweller incorporates an annual calendar – Rolex’s first – a GMT with split 12/24-hour time displays, a COSC chronometer-certified automatic caliber 9001, 100-meter water resistance, abundant dial lume, and remarkable resistance to shock and magnetism.

Caliber 9001 includes a number of innovate features and functions. The 70-hour power reserve helps to avert the constant need to reset the complex calendar. When resetting of the annual calendar display is necessary, it can be done using a combination of the “Ring Command” bezel and the crown. The bezel engages the different setting functions of the watch while the crown remains in a static position to regulate the time, date, and month displays.

In addition to this Rolex, tonight’s show includes the Audemars Piguet Millenary 4101, the Ulysse Nardin Sonata, the Blancpain Fifty Fathoms Tribute to Mil-Spec, and the Jaeger LeCoultre Master Ultra Thin Jubilee.

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