Over the last decade, Oak & Oscar and the Windup Watch Fair have grown up together. We had a booth at the very first Windup in NYC, and we’ve been honored to be a part of it ever since.

With Windup’s tenth year winding down this week, we decided to put our watchmaker’s coats on and cook up something special for the 2025 edition of Windup NYC to conclude an exciting year in watches.

The Olmsted Windup edition commemorates ten years of both Oak & Oscar and Windup with a special dial and caseback engraving done right in our Chicago HQ.

Only five of these watches will be offered to the public and are available exclusively at Windup NYC. Chase will be on hand at the Windup Watch Shop booth on Saturday, October 18th from 12-2pm.

Come by, say hello, and add something really special to your collection!

We live by the credo of making no little plans and we're always pushing our horological and manufacturing capabilities. Celebrating 10 years with the Windup Watch Fair felt like a fitting time to put ourselves to the test and try something new.

A classic, automatic winding, 38mm field watch with a two-layer sandwich dial, screw down crown, and inner minute track with orange cardinal numeral accents.

The Olmsted 38 takes its namesake from conservationist and founder of landscape architecture, Frederick Law Olmsted – an avid believer in the need of natural public space in society. Olmsted is responsible for designing many of the public parks in the United States; notably, Central Park in New York City, and Jackson Park in Chicago.

Just five examples of the Olmsted Windup Edition will be available at the Windup Watch Fair for $1850 on a stainless steel bracelet.

Yup, our trip to Windup NYC back in 2017. We'd just launched the Jackson — a flyback, column wheel chronograph and it was a blast showing it off to all the crowds! Check out the video by clicking the image above!