The past ten years have been a wild ride! Click to read all about the early days of Oak & Oscar, how far the brand has come this last decade, and where we're headed from here!

The Windup Watch Fair just wrapped its tenth year. At the recent NYC edition of the Fair, they hosted a panel discussion that brought together many of the brands that were at the very first Windup, including Chase! Click the story to find out what it was like ten years ago and how the industry has changed over the last decade!

A very very rare bottle of Very Very Old Fitzgerald privately bottled for the Blackhawks-owning Wirtz family just sold at auction for a staggering price with the proceeds benefitting the Blackhawks foundation! Read on to find out more!

Oscar wasn’t just a mascot — he was family. We recently said goodbye to our loyal shop dog, greeter, and namesake, and while the HQ feels a little quieter, the memories (and pawprints) he left behind are everywhere. Here’s to the goodest boy, and the heart behind Oak & Oscar. ❤️🐾

The 2025 Oak & Oscar Owners weekend was a blast as we celebrated our 10-year anniversary with the best group of folks on the planet! Read the story to check out the highlights of this year's event!

British lifestyle magazine, City AM, just published a piece on the surprising connection between watches and your favorite beverages. The Olmsted FEW was featured amongst a stellar list of watches. Read on to find out more!

We're offering a limited batch of Big Eye's featuring our special 10-year logo to celebrate our 10-year anniversary. Read on to learn more!

We made five limited edition Olmsteds to celebrated ten years of Oak & Oscar and the Windup Watch Fair. Check out this special piece we made to commemorate the occasion!

Nick Lehner of StrapHabit just went hands-on with the Humboldt GMT! Read on to learn more about his thoughts on this true strap monster!

Our 10-year celebration continues with a highly limited release of special edition Humboldt 12-HRs in grey! Click the story to find out how to enter this month's lottery!