Five watches. Ten minutes. But that's not what made the Humboldt GMT 2026 Chicago Edition a success. Created exclusively for Windup Chicago, this five-piece release celebrated our hometown and the incredible community that gathered around it.

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It's the holidays, and if you're struggling to find what to get the watch lover in your life, Chicago Magazine and Oak & Oscar have you covered! Continue reading

We had a blast at the 2024 Chicago Windup Watch Fair! Read on to hear about how folks responded to seeing the Atwood in the metal, our meetup at Goose Island on Friday, and a special appearance by none other than Oscar himself! Continue reading

"A local brand connection, clever use of materials and free whiskey? This is how you do a proper watch collab, folks." We couldn't have said it better ourselves! Read Gear Patrol's full review of our Olmsted FEW edition to learn more about this unique limited edition watch. Continue reading

The 2023 Annual Owners Weekend was an absolutely fantastic time! Events on Friday, Saturday and Sunday all packed with Owners from across the country. What an amazing time celebrating the phenomenal people that make up the Oak & Oscar community. Continue reading

Oak & Oscar Partnered with SWAG Golf to make a limited-edition, exclusive SWAG Humboldt GMT. Continue reading

The watch community's premier media outlet Hodinkee wrote a profile about Oak & Oscar's journey over the past 7 years, and boy are we excited about it. Continue reading

Nora Taylor, a born-and-bred Chicagoan and Deputy Editor at Hodinkee laid out a great article with lists of watch shops, restaurants, and things to do while visiting the Windy City.

We were honored to mentioned as the "home team" watch brand! 

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