Author Archives: Hiep Nguyen

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The Story Behind the Humboldt GMT 2026 Chicago Edition

Jul 14, 2026

Windup Chicago feels a little different for us. It’s our hometown show, which means we get to spend the weekend catching up with longtime Owners, meeting new ones, and sharing what we’ve been working on. This year, we wanted to bring something special that could only be found in Chicago.

The result was the Humboldt GMT 2026 Chicago Edition.

Limited to just five pieces, this special edition paired everything we love about the Humboldt GMT with a couple of details created exclusively for Windup Chicago. A black PVD bezel insert gives the watch a slightly more understated, tool-watch feel, while the custom Chicago-themed caseback engraving serves as a quiet tribute to the city we’ve proudly called home since Oak & Oscar began.

Everything else remains exactly as it should. The Swiss-made Sellita SW330 automatic GMT movement, anti-shock and anti-magnetic protection, 20ATM of water resistance, a brushed 40mm stainless steel case, bi-directional bezel, and our fully articulated bracelet with a quick-adjust clasp all make it a watch that’s equally comfortable traveling across time zones or heading off on its next adventure.
The five Chicago Editions found five new Owners in about ten minutes, which honestly caught us by surprise.

But if we’re being honest, selling out wasn’t what made this release feel successful.
Success was seeing people stop in their tracks when they spotted the black bezel. It was hearing someone notice the Chicago engraving on the caseback and smile. It was watching conversations start around the table and seeing how many people connected with the idea of creating something that celebrated our hometown in a subtle, thoughtful way.

The watches may have found new wrists in the first few minutes of the show, but seeing how enthusiastically they were received all weekend is what we’ll remember most.

The best part of Windup has never been selling watches. It’s seeing familiar faces, introducing ourselves to people discovering Oak & Oscar for the first time, hearing stories about watches that have traveled the world, and spending a few days surrounded by people who appreciate mechanical watches as much as we do. The Chicago Edition simply became another reason for those conversations to happen.
To everyone who stopped by our booth this weekend, thank you. Whether you picked up one of the five Chicago Editions, tried on a watch for the first time, or simply stopped to say hello, we’re grateful you spent a little time with us.

And congratulations to the five new Owners. We hope your Chicago Edition serves as a reminder of a great weekend and many adventures still to come.

Next

Three Datomasters and a Trip Down Memory Lane

Aug 25, 2026

Earlier today, our friends at Fratello gave us an unexpected little trip down memory lane.

On the latest episode of Fratello On Air, Mike and Balazs were talking about “the watches that got away” — watches they once owned, sold, and maybe wish they still had. One of those was Balazs’s Nivada Grenchen Datomaster.

That brought up a memory we hadn’t thought about in a while.

Years ago, Balazs, Mike, and I all happened to own Nivada Grenchen Datomasters at the same time. Naturally, when we found ourselves together in Basel, during the old school Baselworld fair, we did what any group of watch nerds would do: we put all three together and took a photo. It was officially the largest gathering of Datomasters in the world. Probably.

It’s a small story, but hearing them talk about it again reminded me of one of my favorite things about this industry.

Long before Oak & Oscar had made many of the watches we’re known for today, I was simply a guy who loved watches. I loved discovering them, learning about them, hunting them down and, most importantly, meeting other people who were just as excited about them as I was.

A lot has changed since that photo was taken. Oak & Oscar has grown, we’ve made a lot more watches, and thankfully we’ve still had a few reasons to get together with Mike, Balazs and the Fratello crew over the years.

But the fun part really hasn’t changed all that much.

We still love watches. We still love the stories behind them. And we still really love the people they bring together.

Thanks to Mike and Balazs for the shoutout — and for reminding us of a pretty great one that got away.

Give the latest episode of Fratello On Air a listen: “The Watches That Got Away.”