In 1895,

six cars lined up on a cold, snowy Thanksgiving day for the start of the Chicago Times-Herald race; a 54-mile journey from Jackson Park, to Evanston and back. Nearly eight hours later, after a grueling 7 mph average pace, Charles Duryea’s “motorized wagon” claimed victory and became the winner of the first official road race held in the United States. The legacy of Jackson Park is strong - home of the Chicago World’s Fair, Museum of Science and Industry and the inspiration for our latest timepiece – the Jackson.



The Jackson - Grey

The grey dial model is limited to only 150 pieces.  The classic brushed stainless steel case looks phenomenal on almost any strap combination and is versatile enough to be worn from the boardroom to the track!


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The Jackson - Charcoal PVD

The charcoal PVD is limited to only 100 pieces. The dark case, light colored tachymeter and charcoal grey dial create a striking design that will surely turn heads. The charcoal PVD model will be an instant classic.


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The Jackson - Navy Blue


The navy dial model is limited to only 150 pieces.  The navy dial has a beautiful rich tone with a distinct vintage vibe. The deep dial color, in combination with the classic brushed stainless steel case, lends itself nicely to a plethora of strap combinations. This watch will stand out from the weekend crowd.


  • Manual wound flyback chronograph with column wheel and stacked register
  • 60 hour power reserve
  • Eterna Caliber 39 manual wound 25 jewel mechanical Swiss movement (Cal. 3916M)
  • 28,800 vph / 4 Hz
  • Stainless steel, 40mm case diameter and 14.5mm case height
  • 20mm lug width
  • 46.4mm lug-to-lug
  • Double-domed sapphire crystal with anti-reflective coating
  • Light grey, wrapped tachymeter scale
  • Color-matched date wheel with custom font located at 6 o'clock
  • 5 ATMs water resistance (50 meters)
  • Brushed baton indices with Super-LumiNova BGW9
  • Two-year limited warranty
  • Limited Edition; 150 grey pieces, 150 navy pieces and 100 charcoal PVD pieces 

Watch Includes:

  • Tapered, 20mm Horween leather strap with signed buckle
  • Tapered, 20mm Horween orange leather rally strap with signed buckle
  • Modular leather watch wallet to hold three watches in detachable suede pouches and strap tool. Made of Horween and Tasman leather.
  • Custom American-made strap changing tool

* International buyers are responsible for any customs duties

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"There is something uniquely special about chronographs and we are excited to add such a legendary complication to our lineup."



The Jackson is a 40mm, hand-wound, flyback chronograph with a column wheel. The Swiss-made Eterna Caliber 3916M, has a tremendously strong 60 hour power reserve. The specialized movement utilizes a clever stacked register that provides tracking of both elapsed minutes and hours. An easy to read light grey subdial with alternating five-minute color blocks and color coordinated hands and markers helps the owner to quickly differentiate the elapsed hours (white hand / white markers) and minutes (dark hands / dark numerals).

The 9 o’clock subdial displays running seconds with an orange crosshair dividing the register into three parts. Note that the printed numerals on both registers carry over the same font as the stenciled numbers from the sandwich dials found on the Burnham and the Sandford. The brushed baton indices provide an interesting depth within the dial while capturing the attention of the wearer as the light reflects off the flat surface. The inner groove of the baton indices are filled with Super-LumiNova BGW9 that creates a unique “T” pattern in the dark.

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The color-matched date wheel features a modified font and is positioned at 6 o'clock to maintain balance and symmetry. 

The column wheel, decorated bridges, and engravings can be seen through the sapphire display back. The 20mm tapered leather strap has the perfect orange undertones and will develop a beautiful patina over time.  The Jackson also comes with a custom-made orange leather rally strap. Both straps are made of Horween leather and are hand crafted by Indiana-based Woodnsteel.

The list of details goes on; the highly visible, and true-to-the-brand, orange center sweep seconds hand, color-matched date wheel with custom font, beautifully decorated movement, wrapped tachymeter scale and a couple additional hidden details.  Every component of an Oak & Oscar product is developed and examined with a high level of scrutiny. Details make the design.


The watch is assembled and tested in Switzerland with a secondary round of inspection and testing performed in New York. The final assembly and inspection is completed in Chicago.

Alternating five-minute color blocks and color-coordinated hands and markers on the subdials provide an impeccably legible, easy-to-read design.

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Each watch includes a matching leather watch wallet co-designed by Chase and Dustin, the founder of Woodnsteel. Dustin and his team make the watch wallets using buttery soft Horween leather (the same leather used for the watch strap), protective wool felt and soft grey, detachable Tasman suede pouches. The wallet holds three watches and a strap tool in a compact, flat, portfolio-style case perfect for traveling and storing one’s collection.   But what might be most exciting about the updated watch wallet is the new zippered closure, reminiscent of old-school automotive manuals, and the new interior pockets that can hold anything from extra straps to a passport.

want more straps? 

We've got you covered. 

Check out our selection of accessory straps in some pretty amazing colors!