$20,000 Watches I Love From Rolex, Audemars Piguet, Jaeger LeCoultre; The Best Men's Watches at $20K

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