The Goodest Boy
We said goodbye to Oscar last week and it’s hard to put into words just how much he meant to me and my family. He was my buddy. Always there with a smile, a nudge, and that calm, happy presence that could make any day better. The shop feels quieter without him, but I’m grateful for all the years we had together and the countless memories he left behind.
We first brought Oscar home from Wisconsin years ago. My wife and I were supposed to drive up early morning on March 18th, but a massive rainstorm washed out the roads and delayed us for hours. We weren't sure if we'd be able to get him that day. But luckily the roads cleared up and we made our way north, excited and a little nervous. It was our first living creature to take care of — our first kid really!
Those first few weeks were rough. He hated sleeping in his crate, and no one got much rest. We tried sleeping next to it, talking to him, anything to calm him down. Eventually, we gave up and let him sleep in our bed. That night, he slept through the night like a champ. He curled up between us, perfectly content. From that point on, he was part of the pack and cemented his spot on the bed.
Oscar was endlessly friendly. He wanted to say hi to everyone and loved carrying a stick on his walks, tail wagging like he owned the block. He only ever destroyed one book, and, fittingly, it was about watches.
As he got older, his puppy energy never really faded. He just got taller and better at counter-surfing. No kitchen was safe. He even figured out how to open the trash can… and when we moved it inside the cabinet, he figured that out too.
When I was dreaming up a yet-unnamed watch company, I kept thinking about the things that mattered most to me: family, bourbon, and dogs. In fact, my first word was my dog's name, "Jesse." One night, sitting on the couch with Oscar next to me and a glass of bourbon in hand, it just clicked: Oak & Oscar. That moment, that feeling — it was everything I wanted the brand to represent. Warmth, loyalty, good company, and a sense of purpose.
Oscar became a fixture at the Oak & Oscar HQ. He greeted guests, barked at the UPS driver, and reminded me to get up and take walks when I’d been glued to the desk too long. He loved sitting next to me at my desk or laying down on the rug. He was always by my side.
He had his quirks, of course. Trash cans needed lids, snacks needed hiding, and the couch had an official “Oscar spot.” If someone sat there, he’d sit at their feet and stare until they moved. Once they did, he’d hop up, get cozy, and expect head pats from his new seatmate. He also had a favorite toy that an Owner gave him years ago. He’d search it out every time he came to the shop, ready for a few rounds of fetch. Thankfully, the "squeaker" inside broke years ago.
Oscar's been part of numerous photo shoots, magazine spreads and was even featured on the local news! Luckily he never let his fame go to his head.
We just hosted our annual Owners Weekend and I had my fingers crossed he'd be able to join us. We had over fifty folks packed into HQ; sharing food, bourbon, and plenty of laughs. And thankfully, Oscar was right in the middle of it all. He worked the room like a pro, soaking up every pet and scratch behind the ears. You could tell he loved being the host. It was classic Oscar. Happy, calm, and surrounded by people who adored him. He couldn't get enough head scratches!
Guests and Owners always loved having him around. There was something about Oscar that instantly made the shop feel more like home. He had a way of making folks feel more comfortable. He made connections easier, and I think people saw that same spirit in the brand itself. It’s part of why we support One Tail at a Time, our local dog rescue. Oscar made that mission personal.
Oscar taught me a lot. Patience, perspective, and how to appreciate the small things. He reminded me to slow down, take a breath, and enjoy the moment. He showed me what loyalty really looks like and how a little joy can go a long way.
He wasn’t just a mascot. He was family. He made tough days easier and good days even better. I’ll miss him deeply, but I’m so thankful for the time we had together and the impact he’s had on all of us.
Here’s to the goodest boy. I love you and miss you little buddy.
— Chase
