Oak & Oscar: The First Ten Years

Dec 04, 2025

The past ten years of Oak & Oscar have flown by! From a scrappy upstart at the early days of the so-called “microbrand” movement to an established independent brand with its own in-house watchmaker and several signature models under its belt, Oak & Oscar has grown in unexpected ways, and we’re here to stay.

Many of you may have heard bits and pieces of Oak & Oscar’s origin story throughout the years, and if you’ve been along for any part of the journey, you may know a little bit about what’s gone into making the brand what it is today. But, as we reflect on the past decade, we wanted to offer a more comprehensive account of our story thus far, give you some insight into where we’re going, and share some rarely viewed, behind-the-scenes photos from the Oak & Oscar archives. Below, for example, you can see an early rendering of the Burnham as we explored the design of our custom sandwich dial numerals.

The brand officially launched in 2015. But the idea of Oak & Oscar had been simmering in Chase’s mind for some time before it actually got off the ground. “I was toying with the idea up until I started the brand,” Chase said recently. “It was years in the making. I kept asking myself, ‘Can I do this? Maybe!’ So I started playing around with ideas, doing some budgeting, and things like that. I’d put it down when I was busy and then pick it up and dive deeper into it. I had to consider who I would work with in terms of suppliers and think about different strategies for various aspects of launching the brand.”

The name was easy. With bourbon in hand and his best friend, Oscar, beside him, Oak & Oscar just clicked as a reflection of things he enjoyed and cared about. You can read more about the origins of the name here.

Of course, a big part of launching a watch brand is being passionate about watches! Chase had always been interested in watches. You can hear him discussing his fascination with his first Timex and its waterproof capabilities on the Tenn and Two podcast back in 2020 and on the Watch Society podcast earlier this year!

There’s a ton that goes into starting a business that you may not think about off the bat. And it may even require a certain naivete. As Chase put it during our recent chat, “If I were to think about starting a brand right now, I’d probably say it's a terrible idea. For one, the space is way more crowded now. The costs have increased with tariffs, among other things. And it's frankly just a huge risk. But, back then, it felt like the right thing to do, and I’m super glad I did!” There are budgets, and designs, and suppliers to look into. But what really lit the fire was the idea of making a great watch. “The passion for the brand and the product had to come first. All the boring stuff like taxes and paperwork came after.”

Chase adds that he had to find people that were really good at what they did in order to make this idea a reality. "I wanted to make sure that I was working with great quality makers and suppliers.” There’s a lot of trial and error, too. It’s a matter of trying out different suppliers and ways of doing things until you find the right fit. Discovering the best person for the job will allow the vision to develop. Sourcing leather for the straps was a no-brainer with the Horween Leather Company just down the street.

But finding the right person to craft those hides into straps was a different story. “We went through two or three different strap makers until we landed with Dustin at Woodnsteel.” Below, you can see an early sketch for our OEM straps you now know and love!

Starting your own company is a huge risk. There’s only so much forecasting you can do before you just have to put your idea out there and test it out. Luckily for us, Oak & Oscar has grown into a longstanding brand with many loyal Owners across the globe. But there was no guarantee of that back in 2015.

Don’t forget that, especially at that time, people were somewhat skeptical of the microbrand space. There was an assumption that smaller, independent watch companies couldn’t possibly produce a quality timepiece that rivaled more established (and more expensive) brands. But through our dedication to our craft and a supportive community of enthusiasts, we proved a lot of folks wrong. The industry looks much different these days, and we're proud to be at the forefront of it along with so many other great brands!

Over the years, we’ve refined the process of designing, producing, and selling watches. In the early days, though, Chase was running the show all by himself, packing and shipping watches from his Chicago apartment.

The launch of our very first watch, the Burnham, was especially nerve racking. Chase had just had his first son, and he was still working a day job, all while trying to get the brand off the ground in his spare time. As you can see from the photo above, it was a bit of a chaotic time! Balancing family life, work, and launching the Burnham was a challenge, to say the least! But the excitement of showing off the watch for the first time made it all worth it. And yes, the very first round of Burnhams were packed and shipped right from Chase's kitchen!

The success of the Burnham solidified Oak & Oscar’s place in the burgeoning independent space. But the sequel had to deliver a real bang. The Sandford did not disappoint!

The design of the Sandford was inspired by Chase’s love of travel. “I lived in London for a while when I was younger, and I was always wondering what was going on in the US. And then when I moved back, I was always wondering what was going on in London. So a travel watch was really important to me.”

With its dual crowns, 24-hour rotating inner chapter ring, and arrowhead-tipped GMT hand — you can see an early sketch for the design above — the Sandford pushed Oak & Oscar’s design language to the next level. Jason Heaton wrote in his 2016 hands-on review of the watch that, “the Sandford avoids the dreaded sophomore slump that afflicts so many, from musicians to athletes to M. Night Shymalan movies. It is a watch that shows the focus on individuality and the quality of its designer while setting itself apart from so many derivative homage watches in off-the-shelf cases.”

With two solid offerings under its belt, you might think that Oak & Oscar would rest on its laurels and coast along with old designs. But then you wouldn’t know anything about Oak & Oscar! For the brand’s third watch, we went big with one of our most popular models of all time, the Jackson, a column wheel flyback chronograph with a unique bi-compax design featuring a stacked register at three o’clock. The Jackson required some innovation and an expansion of our watchmaking partners to an expert team in Switzerland.

We always strive to “make no little plans.” Chase notes that, when it came to developing the Jackson — in the prototype image above, you can see that the watch was originally codenamed the "Boulton" — "I knew I needed a team that had been doing this for years. We wanted to keep challenging ourselves and showing people that we mean business.” The Jackson was a serious offering for lovers of chronographs that offered a unique movement in the manually wound Eterna Caliber 39 with distinctive design choices that set it apart in a crowded market.

Design is a key element of what we do. James Stacey once wrote that all of Oak & Oscar’s creations are “meticulously detailed." And we carried that ethos forward in 2021 with the evolution of the OG Jackson chronograph into the quirky, asymmetrical Big Eye.

Importantly, we want to make great watches, but we also want to make fun watches. And the Big Eye “strikes the right chord of vintage quirkiness.” Of course, there are practical reasons for having an enlarged register at three o’clock (the eponymous “Big Eye”) — increased legibility, for one — but at the end of the day, “the Big Eye is just fun!”

Some designs, however, are more understated but no less significant or interesting. Debuting in 2018, our next watch after the Jackson was our first true adventure watch, the Humboldt 12-HR. Each watch in the collection fulfills some sort of need or performs some important function. That sentiment prompted the design of the 12-HR. “I wanted a great kind of adventure watch.” With the 12-hour bezel, you can use it as a GMT ‘lite’ if you will.”

The Humboldt also marked a couple of huge milestones for the brand. It was the first of our watches to be offered on a steel bracelet. But perhaps most importantly, it was Oak & Oscar’s first non-limited production model watch!

It was a crucial step both for the success of the brand and for aspiring Owners to be able to have a watch in stock at all times that folks could pick up whenever they wanted. “We spent so much time and so much effort crafting and perfecting the tiny little details in every design. To spend that amount of time and then sell only 3-, 4-, 5-, 600 watches, and then they’re done forever? That’s hard. And we were also in this position where we would sell watches for a few months, and then literally for the rest of the year we’d have nothing.”

The Humboldt 12-HR quite literally ushered in a new era for the brand. Folks who wanted an Oak & Oscar were no longer subject to the whims of how quickly their browser refreshed during limited edition drops!

Now, Oak & Oscar has three production models in the signature collection — the Olmsted, the Humboldt GMT, and the Atwood — even as we continue to design some really cool limited editions. Our design ethos is always forward-looking as we endeavor to test our technical, horological, and design skills.

The Olmsted debuted in 2019 and marked the return of a versatile field watch to the collection. With a "Goldilocks" 38mm case size, drilled lugs, 100m of water resistance, and a clean, balanced design, the Olmsted is the perfect everyday watch. Check out highlights from our trip to Switzerland to oversee production here!

The Humboldt 12-HR was retired in 2022 and evolved into the GMT with anti-shock and anti-mag technology: the perfect adventure watch. And, in mid-2024, a chronograph returned to the line-up with the Atwood! Pushing ourselves to the limit once again, we managed to develop another unique, manually wound, column wheel flyback chronograph all in a svelte case that's just 12.9mm thick. You can learn more about the production process of the Atwood here.

The brand has grown by leaps and bounds over the years. We've come a long way since Chase was packaged up the Burnham in his apartment for our first crop of Owners!

In 2020, Nathan Bobinchak came on board as our director of watchmaking. Having our own in-house watchmaker has allowed us to expand our horological horizon. We've produced some incredibly cool pieces like the Humboldt Seven Year. Produced for the inaugural Chicago edition of the Windup Watch Fair, the Seven Year featured bezels that were hand-machined by Nathan out of a special brass alloy. To make the bezels, he employed the use of a vintage Derbyshire Elect lathe that used to maintain timepieces in the U.S. Naval Observatory. The Derbyshire has since been retired, but we've got new one in the shop that we're using to do even more cool stuff!

In 2023, Greg was brought on (Hi! 👋) to help manage the shop and deliver all the editorial goodness you're currently reading.

So what does Oak & Oscar have in store for the next decade? We're going to continue to grow our amazing community of Owners and find new ways to engage with them, like our awesome Built to Discover trips!

We’re going to keep making awesome, durable, wearable watches. We’re going to experiment with materials. We’re going to test our limits and see what we can do both in-house and with our amazing partners. For example, we just acquired a shiny new laser that we're using to do everything from cut dials to engrave casebacks.

We’re going to explore new complications. And we’re going to keep making more watches for more people at a range of price points. So, stay tuned! You won’t want to miss what we do next!

Photo Report

It's hard to include ten years of history in one article. So enjoy a short photo report featuring some images that capture what it was like when the brand first launched and how it's grown and evolved over the years!