Like aviator shades and shearling jackets, the best pilot’s watches for men are classics that trace their lineage directly back to the cockpit. The original 1904 Cartier Santos is considered by many to be the first example of the genre, but the look of the pilot’s watch as we know it today was popularized in the ‘40s by brands like IWC, A Lange & Söhne, and a handful of others. From the outset, pretty much every pilot’s watch had three things in common: a dial with big, ultra-legible markings; an oversized crown (pilots needed to be able to adjust it without taking off their gloves); and an extremely robust case (essential when you’re pulling Gs at 30,000 feet.) But the next major twist in the pilot watch story arrived roughly a decade later, with the debut of one of the most legendary timepiece collabs in history: the Rolex GMT-Master. Tasked with imagining a new kind of watch for Pan-Am airline pilots, Rolex added a distinct red and blue bezel to help keep track of multiple time zones at once—and the rest, as they say, is history. Today, of course, you don’t need Rolex money to get your hands on a great-looking aviator’s watch. All of the budget-friendly selects below will add a dash of high-flying style to your fall fits, helping you channel Tom Cruise at his Top Gun best in the process.
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