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Oak & Oscar’s The Jackson Flyback Chronograph Wristwatches

A hand-wound piece of exceptional merit from the Chicago-based brand

In the watch world, brands like Oak & Oscar make it easy to be excited about boutique horological designers. Their latest piece, The Jackson, represents both ambition and cohesion. This limited edition 40mm flyback chronograph carries plenty of technical complications—many of which pose big challenges for smaller watchmakers. This was alluring to the brand’s founder Chase Fancher. But beyond the chrono function, stacked hands and 60-hour power reserve that he included, this hand-wound mechanical piece (in three styles) has so many secrets—they are nuances really, that will unfold with time, but everything has meaning. Oak & Oscar’s watches are all limited edition models, and the previous two releases have long since sold out. The Jackson is the latest opportunity to own a piece and, depending on what one looks for in a watch, it might just be their best option yet.

“The Jackson is named after Jackson Park on the south side of Chicago,” Fancher explains to CH. “It’s where the nation’s very first car race took place in 1895. The starting point was in Jackson Park. They drove to Evanston and back.” With the knowledge of its car inspiration, one makes further note of the automotive influence on the watch design. A thorough analysis of the piece also reveals its connection to the others from the brand—while all three are distinct, they clearly hail from the same family. That said, the Jackson is the brand’s first chronograph. “It just felt like a good progression from a three-hand date and GMT with rotating bezel,” he continues. “It’s arguably one of the sexier complications. Add to it that it’s got a stacked register—two in total, not three—it’s my vibe and aesthetic. It’s what I love. That’s where this comes from.”

With a piece in hand, it’s quite easy to notice Fancher’s appreciation of balance. From weight to symmetry (and subtle variations), the watch offers a precise, organized beauty. And still, it pops. “I love navy, and oranges and greys,” he continues, “It literally does translate into everything I do. I don’t really like black leathers. I wear brown leathers.” This is all evident in all three styles. “Oak and Oscar as a whole, the design language involves all of this but with depth—including depth on the dial—it’s its own little city in there. I love the idea of that,” he concludes. And while design matters, there’s an Eterna Caliber 39 manual wound Swiss movement ticking away inside and a tachymeter wrapping the dial up like a ribbon. It’s a functional delight.

You can purchase The Jackson from Oak & Oscar’s online store, where the Navy and Grey versions currently sell for $2,650 and the PVD for $2,850. These are limited pre-sale prices.

Images courtesy of Oak & Oscar


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