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The history of the pilot's watch is nearly as old as men's wristwatches themselves. Back in 1911, a couple of guys you may have heard of named Cartier and Jaeger began selling the watch they designed for Brazilian aviator Alberto Santos-Dumont to allow him to keep time with both hands on the controls. The aviator's watch as we now know it, with a black dial and simple white numbers, dates back to the A-11 design from 1943—and while modern interpretations are generally larger and more accurate, the best-looking and most readable remain those closest to the original high-contrast formula. Paired with a fabric strap, per original military spec, an aviator is a near-perfect weekend watch. Left: WWII-era Elgin A-11. Right: modern Maratec Mid automatic.

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