I’m proud of Oak & Oscar. I’m proud of the amazing community we’ve created, that folks purchase our watches to celebrate milestones and that we work with some really amazing people. Everyone’s watch tells a story and it’s an honor to be part of that story.
Small team. Big standards.
Oak & Oscar is an independent watch company. That means a small team, an HQ about two miles northwest of Wrigley Field, and nobody standing between you and the people who make your watch.
We design every watch here in Chicago, and every one is Swiss-powered. Before it ships, each watch comes through HQ for a final quality check from our in-house watchmaker, final assembly and packing. When it's time for a service, it comes home to the same bench.
Being independent lets us make the watches we want to wear, in small batches, and take the time to get the details right. It also means our Owners are part of the story long after checkout. Stop by HQ and see for yourself.
Founder
Founder, capital put-er-upper, risk taker and the guy who makes the coffee and pours the bourbon in the shop. Chase left an unfulfilling corporate job to start Oak & Oscar and find a better work life balance.
He spends his time designing, managing the team and making big plans at our Chicago HQ.
Director of Watchmaking
A classically-trained watchmaker who gave up a life of screens for a life of screws. With official certification from the Swiss American Watchmakers Training Alliance at the Lititz Watch Technicum in Pennsylvania, Nathan has put his skills to work as a bench watchmaker and as a watchmaking instructor for the Horological Society of New York.
As a native Detroiter, he’s excited to bring the art of watchmaking back home to the Midwest.
Creative Director
A typography nerd and Chicago native who has been working in a variety of creative/design roles for the last 2 decades.
Thomas received his first automatic watch as a college graduation gift and has been collecting them ever since.
A fast food enthusiast and a Chicago sports fanatic, he'd happily talk your ear off about the Cubs or which establishment has the best fountain Coke.
Operations
A watch enthusiast with more than ten years of operations experience in the skateboard and surf world, Kevin brings a love for well-made products and thoughtful process to Oak & Oscar. You’ll find him obsessing over the smallest details whether it be a new deck design or dial design.
Outside the shop, he spends his time crafting wood furniture, riding bikes, playing with his dog Lily and passionately talking Chicago sports with anyone willing to listen. A true Chicagoan, it’ll always be Comiskey and the Sears Tower to him.
Chief Mascot
Oscar is the dog that inspired the brand and will furever be our mascot. We lost him in late 2025, and we’re all forever grateful for him.
When Oscar was at the shop, he was either sleeping on the couch, playing with his toy or barking at anyone who even got near the door.
He’d greet you with jumps and butt wags, then settle in on the couch next to you like a true best buddy. No question, he was king around here and knew it!
We believe design can and should inspire.
Since 2015, we’ve partnered with good people to build high-quality watches, watch wallets, and other accessories that are beautiful, superbly crafted, and uniquely Oak & Oscar.
Meet the partners we collaborate with to make your Oak & Oscar timepiece.
That’s why a portion of every Oak & Oscar purchase goes toward helping One Tail at a Time, a local dog rescue committed to providing rescue and adoption services for dogs in need.
