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Hamilton Khaki Field Auto: Hamilton is a storied brand with its roots in the 19th century. While it’s now owned by the Swatch Group and based in Switzerland, it has retained some very cool designs reminiscent of the golden age of American watchmaking. Among the classic silhouettes is this military-inspired piece reimagined in a shade of blue to match your favourite selvedge jeans. Its face is appealingly unfussy, but the coolest thing about this watch is inside: a Swiss automatic movement visible through a sapphire crystal case back. What’s the point of all those magical little gears if you can’t see them whirring away? $945 through www.hamiltonwatch.com.

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Bulova Moon Watch: Quartz watches (the ones powered by batteries, not gears and springs) don’t have the same allure as Swiss mechanical timepieces, but the nicer ones do have the distinction of being more reliable. Bulova was an innovator of quartz timekeeping in the 1960s and 70s, and while they didn’t make the official watch of the Apollo missions (that honour went to Omega), the predecessor to this watch did ultimately make it onto the moon in 1971 on the wrist of Apollo 15 astronaut Captain Dave Scott. Scott’s Bulova sold at auction for $1.5-million in 2015, making the under-$700 price tag on this one all the more appealing. $695 through www.bulova.com.

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Mondaine Evo Big Date: Mondaine is a relatively new watchmaker whose wares are modelled after the timeless aesthetics of Swiss railway clocks. This standout timepiece is quartz-powered, but its unusual looks more than make up for the lack of a Swiss mechanical movement. Anyone who admires the mid-century-modern designs of people like Dieter Rams and Arne Jacobsen will appreciate Mondaine’s clean lines and uber-functional face. Black turtleneck sold separately. $320 (U.S.) through www.mrporter.com.

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Tissot Heritage Visodate: Unlike smoking and sock garters, Tissot’s Heritage Visodate looks just as cool now as it did in the Diefenbaker era. There’s nothing contemporary about the design of this watch (a re-issue of a 1950s model of the same name), but the automatic Swiss movement within is completely modern. Without getting too deep into the intricacies of watchmaking, suffice to say the engine inside this businessman’s special is good enough to be found in a number of much more expensive watches, making it exceptional value. $750 through www.tissotwatches.com.

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Seiko SKX009: Do you know anyone who actually scuba dives? Just curious. I know one guy, and for the record he wears a dive computer on his wrist when he’s in the water. As with off-road vehicles and tennis shoes, however, dive watches aren’t really used for their intended purpose. Instead, their toughness, versatility and nice looks make them ideal everyday watches. As such, Seiko’s SKX009 has a large sturdy stainless-steel case, can transition between formal and casual situations, and has all the hallmarks of classic 1960s design. It also has a robust automatic movement and is water resistant to 200 metres should you actually, you know, ever want to wear one while diving. $795 through www.seikowatches.com.

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