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The 2023 Annual Owners Weekend!

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The 2023 Annual Owners Weekend!

Our Owners are perhaps the most important thing to us here at Oak & Oscar. For us, watches are primarily about the stories and memories shared amongst the members of the enthusiast community. We’ve worked hard to build a welcoming environment for watch aficionados of all stripes. That’s why, every year, we throw a weekend-long party to celebrate the wonderful people that make up the Oak & Oscar community.

People sitting at dinner inside a brewery

This year’s Annual Owners event took place during the weekend of November 3rd-5th. On Friday evening, a group of Owners joined us for a private dinner in the barrel room at Half Acre, one of Chicago’s oldest and best craft breweries. The beer and conversation flowed freely as we talked watches, travel, food, tattoos, and all manner of other things during the course of the night.

People gathered in a room talking and drinking

On Saturday, we welcomed old friends and new Owners alike to our Chicago HQ. The office was packed to the rafters with people who flew in from all over the country to celebrate with us.

Image of magnetic lapel pins with numbers on a steel cabinet

The event gave people an opportunity to peer behind the scenes of Oak & Oscar’s operations, meet fellow Owners, and make new friends. Food was catered by Calo Ristorante, some of the finest Italian cuisine in the Andersonville neighborhood. And, of course, there was plenty of bourbon on hand for Old Fashioned cocktails.

Three men sitting at a table with water and beer in mid-conversation

We saw the remaining 20 or so Owners off on Sunday morning with an F1/football watch party at the Village Tap in Roscoe Village, an old haunt of our founder, Chase. Even for those of us, like myself, who had never seen an F1 race before in their life, it was a great time.

The philosopher in me couldn’t help but order the “Pimento Mori” burger (the name is a play on the latin phrase “memento mori” which translates to “remember you must die”; it’s a reminder to seize the day, or, as we like to say, Make No Little Plans). Our gathering in the beer garden allowed us to continue our conversations from the previous night and keep the party going for just a little while longer.

Image of a grey dial Oak & Oscar wrist watch with leather strap on wrist with a grey sweater

As the name of my burger reminded me, all good things must end. And so, as the race concluded and it gradually became clear that the Bears weren’t going to pull it off, we said our goodbyes and went our separate ways for the time being. But we’re already thinking about next year’s event, and we can’t wait to see you all again! Cheers!

Interested in becoming an Owner and joining us for special events like this? Purchase a watch directly from us and you'll automatically be added to the private list!