n an era dominated by bold claims and grand narratives, Chicago is certainly not blowing hot air for watch enthusiasts. Beyond the shadow of the Windy City’s vast, towering commercial district, a cohort of boutique watch brands has emerged. Among them is Oak & Oscar, a small-scale watchmaker dedicated to crafting high-calibre timepieces not for ostentation, but for authenticity.

The brand’s name beautifully encapsulates its founder’s passions: oak barrel-aged bourbon and his beloved dog, Oscar. Unlike brands that boast of bygone legacies or ego-driven owners, Oak & Oscar radiates a sense of humility at its core. Chase Fancher, the self-proclaimed “capital put-er-upper” of the company, embarked on this journey with an unbound idea: to build a business around the things he cherishes. “Oak” and “Oscar” are just symbols of that vision.

Oak & Oscar founder Chase Fancher

As we delve deeper into the brand’s story, it becomes apparent that the company is about more than whiskey and dogs. What began as personal anecdotes has evolved into a community of owners, tales of adventures, collaborations with the USA Curling team, and an expanding footprint in the craft of watchmaking. Oak & Oscar’s timepieces are tailored for modern-day explorers who connect with, and sometimes become, the stories interwoven into its world.

Since its inception in 2015, Oak & Oscar has garnered attention for its fresh design language, meticulous attention to detail, and robust build quality. The first three limited series quickly sold out and won critics over. Then came the Humboldt in 2018, which marked the brand’s foray into serial production, solidifying its position as a rising star in a competitive field. With every annual product launch, Oak & Oscar has continued to gain popularity through word-of-mouth.

The Olmsted 38 is named after Frederick Law Olmsted, father of landscape architecture and designer of many of the public parks in the United States; notably, Central Park in New York City, and Jackson Park in Chicago.

However, in the volatile microbrand segment, many newcomers appear and disappear, leaving behind generic products. Fancher thus sets his brand apart by employing premium materials and unorthodox transparency of its suppliers (the latter warrants a dedicated page on the brand website). The watches are made in Switzerland, in partnership with a Biel/Bienne manufacturer, using high-grade ETA or Sellita movements and US-sourced artisan leather.

Oak & Oscar partners with local artisans and the oldest continually running tannery in the nation to produce its premium leather watch straps.

This approach has resonated with watch enthusiasts. Fancher emphasises, “We’re passionate about making our mark in horology with timepieces that respect the craft. We’re not in this to make fashion watches or a quick buck. Our watches are a cut above what they’d typically expect from a small American brand. Our team and I are here for the long haul, and I think people recognise that.”

The brand’s commitment to excellence is reflected in its premium pricing, with Oak & Oscar watches currently sitting between $1,500 and $2,500 for signature three-hand and GMT models like the Olmsted and the Humboldt. As the brand evolves, Fancher has clear intentions of exploring more intricate, in-house tailoring and custom complications. He envisions higher-end offerings that translate to deeper levels of design and craftsmanship.

The latest Humboldt GMT Titanium is packed with adventuring capabilities: Swiss-powered, anti-shock, anti-magnetic, GMT functionality, bidirectional 24-hour bezel, with 20 ATM of water resistance. A ’go anywhere, do anything’ watch that is built to discover.

Fancher spent years finding the right supplier skilled enough to make canvas watch straps that are durable and rugged for all kinds of outdoor conditions.

Fancher seeks to develop the brand by tapping into its internal capabilities and pushing the team’s abilities, rather than following external market trends. In an unusual move for a US microbrand, he has brought on board a homegrown certified watchmaker. This has resulted in technically astute timepieces. Select bezels and components are also handcrafted on site using a lathe. The workshop could potentially extend its capabilities to gear cutting, wheel fabrication, and features like bespoke bevel edges and hand-blued screws.

The prospects of more localised production excite Fancher, who remarks, “We’re building the technology and capability to do what we think is fun.” That said, he has no desire to hinge on an American identity or capitalise on the resurgence of American watchmaking, asserting, “We are a global brand.” Given its Midwestern values, leaning on the Swiss-made stamp would also seem out of place. It’s a conundrum that many US watch companies have to grapple with.

A true Oak & Oscar mantra is “Make No Little Plans”, a quote from the late Chicago architect Daniel Burnham.

Nonetheless, Oak & Oscar possesses an undeniable soul. Fancher elaborates, “What folks truly gravitate towards is our absolute authenticity. Everything we do is very much of our own world. Our watches seem like they’ve been around for decades. But they have their modern language and unique character; no one can claim they are a derivative of something else. We stand behind our product, and that’s what people really connect with.”

Eager to share their product ethos, Fancher explains, “Our mentality in the design is rooted in watches that are built to discover – be it on a trip overseas, camping, fly fishing, or even in the intellectual sense, like a scientific discovery for curing cancer. The idea is about that kind of pursuit of knowledge and experience, and it’s not so much about creating that fancy dress watch.” Collectively, this in turn expands the Oak & Oscar world in rich and unexpected ways.

A hallmark of Oak & Oscar watches is its use of the sandwich dial to create an architecture that is built for legibility.

With that in mind, Fancher encourages watch owners to embrace his timepieces fully. He says, “Go out there and use them, scratch them up, have them cleaned off from all the dirt.” Each scuff on a watch is a story, a shared badge for the Oak & Oscar community, one that values more than just the craft of horology. These watches are chronicles of life’s indelible moments, enriched by the personalities who wear them and the stories they tell.