Introducing The Oak & Oscar Jackson Big Eye Flyback Chronograph

Our friends in Chicago have remained productive over a tumultuous year, with the release of their Olmstead Matte late last year, and today, they reveal a new limited edition Jackson that is sure to raise a few eyebrows. The new Jackson LE isn’t just any chronograph, it’s a hand wound, flyback chronograph with a “big eye” dial design. Oh, and it’s dateless. Queue the Vince McMahon reaction meme here. All this is dressed in the very American classic Oak & Oscar design language that is direct, practical, and not without a surprise or two to be discovered.

The Jackson Big Eye is built within a 40mm fully brushed steel case with a very manageable lug to lug measurement of 46.4mm. Thickness is kept in check thanks to the hand winding movement, meaning a 14mm case height, and 14.5mm including the double domed sapphire crystal. In all pretty respectable numbers for a watch with this level of complexity and at this price point. 

Oak & Oscar is using an Eterna caliber 39 for the Jackson Big Eye, which is hand wound, and brings flyback functionality to the chronograph. It uses a column wheel actuation and stacks the minute and hour recording hands atop of one another in the Big Eye sub-dial at 3 o’clock. The movement is decorated in a manner similar to that of other Oak & Oscar watches we’ve seen, meaning clean and tidy with little in the way of ornate. The 4 stars make an appearance on the striped bridge, a hallmark of the brand since the beginning.

Things get interesting on the dial side of the Jackson Big Eye, most notably from the oversized register at 3 o’clock, but also from the restrained colorway of the matte grey dial and sparse orange accents. The oversized register gets a light grey base with dark grey and orange detailing that offers a lot to take in, without feeling overwhelming. This timing register tracks elapsed minutes with a long dark grey hand, and elapsed hours with a shorter white hand, against white markers. The whole register is split into three quadrants with thin orange lines, a theme repeated within the running seconds sub dial at 9 o’clock. 

The rectangular hour markers are applied with a helping of lume at their tip and bisecting the marker as a whole, creating a two-toned appearance that dominate the otherwise sparse dial. The Oak & Oscar logo and Flyback label appear at 12 and 6 o’clock, but there’s an easter egg hidden above the Flyback label, with the same “O” logo mark you see at the counterweight of the timing seconds hand, mirrored on the dial perfectly underneath the hand at rest. It’s subtle, but it’s a theme we’ve seen since the very first Oak & Oscar. The seconds hashes appear in orange at the very edge of the dial adding a bit more depth upon closer inspection, and a tachymeter scale is rendered on the sloping rehaut. 

This is a very handsome watch that only reveals more little details to enjoy the closer you look. All that fades away at a glance, though, allowing for a practical and legible dial that should stand up to everyday usage. Just 50 Jackson Big Eye watches will be produced, and each will be priced at $3,150. That price includes their lovely Horween watch “wallet” and a pair of Horween straps (one rally style). Oak & Oscar.

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Blake is a Wisconsin native who’s spent his professional life covering the people, products, and brands that make the watch world a little more interesting. Blake enjoys the practical elements that watches bring to everyday life, from modern Seiko to vintage Rolex. He is an avid writer and photographer with a penchant for cars, non-fiction literature, and home-built mechanical keyboards.