Oak and Oscar Watches

Oak & Oscar Watches

Oak & Oscar is American indie watchmaking done right — small-batch releases, thoughtful design, and a founder who actually listens to the community. No fluff.

No venture-capital hype. Just purpose-built mechanical watches with Midwestern soul and collector cred.

If you’re into wearability, authenticity, and quiet excellence, this is one of the smartest buys in the game.

A Little History

Oak & Oscar was founded in Chicago in 2015 by Chase Fancher, a former corporate guy turned watch entrepreneur who wanted to build modern tool watches with a design-first

mindset — and build them in a way that actually respected the people who buy them.

The brand’s first model, the Burnham, set the tone: 42mm, clean sandwich dial, hand-wound movement, limited run. It sold out fast. Since then, Oak & Oscar has stayed lean

releasing just a few models each year, all assembled in the U.S., with Swiss mechanical movements and custom tooling sourced from American partners whenever possible.

It’s not about chasing trends. It’s about making the kind of watch you actually want to wear every day.

What Collectors Love

Oak & Oscar has built a cult following among design-minded collectors, thanks to:

  • Excellent proportions — most watches in the 38–41.5mm range

  • Sandwich dials and matte textures — for legibility and depth without flash

  • Custom casebacks — often engraved with maps, movement diagrams, or city nods

  • American-sourced extras — Horween leather straps, handmade wood boxes, etc.

  • Great community engagement — Chase is active with customers, collectors, and feedback loops

Key models include:

  • Jackson Chronograph — flyback chrono with column wheel, triple-register layout, and awesome wrist feel

  • Humboldt GMT — clean traveler’s watch with 24-hour bezel, screw-down crown, and 200m WR

  • Olmsted — field/dress hybrid in 38mm, super legible and wearable

  • Sandford and Burnham — earlier models now considered cult classics

Movements are typically ETA or Sellita-based, but regulated and tested in-house. Recent chronos have used Eterna or Concepto flyback calibers, with sapphire backs to show

off the goods.

Why Oak & Oscar Deserves a Spot

Because it’s a brand that gets what collectors actually care about — great design, perfect sizing, solid mechanical execution, and a buying experience that feels personal.

You’re not buying some private-label watch with a slapped-on logo. You’re buying something that’s been designed, prototyped, tested, and refined by a team that lives

and breathes the enthusiast space. And when it lands on your wrist, it feels like it was made for you.

Plus, the resale value holds up surprisingly well for an indie — which tells you a lot about the fanbase.

What’s Out There Now

Oak & Oscar’s lineup evolves slowly — most models are limited runs:

  • Jackson Chronograph — 40mm, flyback function, column wheel, manual wind

  • Humboldt GMT and Field — 39.5mm, 200m WR, travel-ready

  • Olmsted 38 — 38mm, screw-down crown, sandwich dial, workhorse automatic

  • Limited Editions — including navy dial runs, gray-out cases, and charity collabs

Prices range from $1,500–$3,000, depending on model and spec. Pre-owned pieces tend to move quickly, especially Jacksons and early Burnham releases.

Fed’s Take

Oak & Oscar is one of my favorite modern American brands.

Every watch I’ve handled has been thoughtful, well-built, and ridiculously wearable. The finishing is sharp, the straps are excellent, and the whole experience — from the box

to the handshake — feels curated. You’re not just buying a watch. You’re joining a crew.

If you want indie charm, tool-watch specs, and community-backed design, Oak & Oscar delivers every time.

Check Out Our Oak & Oscar Inventory

Delray Watch is always on the lookout for unique Oak & Oscar watches — especially Jackson Chronograph, Olmsted, and limited edition Humboldt models.

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