The Cultivated Wrist

This week, we’re taking Pilot’s watches, and not the kind from IWC (well, maybe a little bit). There’s no commonly agreed upon definition of what a watch needs in order to be considered a pilot’s watch, we can say a few things about them with certainty. The term comes from watches that were issued to WWII pilots, and the traits you’d find on some of those models have carried through to modern executions. Original Pilot’s watches were large, as in 50mm or more large, and generally worn over jackets or gloves. These days, brands are pretty liberal in their interpretations of Pilot’s watches, but they generally need to be clearly legible at a glance, which means oversized hour and minute hands, and more often than not, a large marker at 12 o’clock on the dial for orientation. Below you’ll find a selection of modern Pilot’s watches available on StockX, and what sets them apart.


We can’t start this list without an IWC Pilot’s watch, but we’re going with the accessible, ever fashionable, and easily wearable Mark XVIII. This is a watch that takes all the great components of historic Pilot’s watches and filters them into an eminently wearable three-hander. The large hands dominate the flat black dial and a practical date window makes a subtle appearance at 3 o’clock. Measuring in at 40mm in diameter, this is a watch that’ll fit nearly any wrist, and look good doing so. Best of all, this one won’t break the bank. There’s an Ask of $2,800 on this example right here.

Bell & Ross Military WWI 92

Bell & Ross is known for their watches designed after cockpit instrumentation, that is to say, with square cases. They went a more traditional route with their Military Vintage WWI watch, opting instead for a more literal interpretation of watches issues to fighter pilots during WWII (despite its WWI naming convention). The round case measures in at a period correct (ish) 45mm and the dial design is pure old school. A large minute track with 5-min increments dominates the outer reaches of the dial, with a smaller hour ring running along the inside. Oversized hands make for easy legibility and the iconic triangle with two dots resides at 12 o’clock. This one’s also wallet-friendly with a current Ask listed at $2,000.

Rolex Sky-Dweller

The Sky-Dweller is a bit of an anomaly in this grouping, but it’s a traveler’s watch to be sure so we’re running with it. The Sky-Dweller features Rolex’s Ring Command system, which means the setting functions of the crown can be selected for via the rotating bezel. Complications include a second time-zone display, a calendar function, and a date. With the introduction of a steel/white gold variant of the watch in 2017, the Sky-Dweller is now more accessible than ever (compared to the first variants, at least). This example with blue dial has an Ask of $22,000.

Oris Big Crown Altimeter

The Oris Big Crown Altimeter is a thoroughly modern take on a Pilot’s watch, taking a clean sheet approach to its design and functionality. The result is a fresh take on the genre that embraces old-world practicality like oversized hands, large numerals, and a large case (47mm!) while welcoming modern styling and oh yeah, a built-in altimeter (did the name give it away?). The crown at 4 o’clock allows users to set their baseline altitude to subsequently get a read on the changing altitude during a trip. The feature can be especially useful for use in small planes or even mountaineering or hiking at altitude. If you don’t fall into any of those categories, it’s still a great conversation starter. This example has an Ask of $2,000 at the moment.

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