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2023 Year In Review

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2023 Year In Review

It’s been a big year at Oak & Oscar! With several watch releases, a slew of incredible events, a new addition to the team (Hi!), and so much more, we have a lot to celebrate. This year saw a few exciting brand collabs, charity events, experimental pieces, our inaugural Built to Discover trip, and a new titanium model, among other big news. Read on to find out more about what we’ve been up to this year!

From the Bench

image of watchmaking in process

We take the history and craft of horology seriously at Oak & Oscar. And we love nothing more than sharing our love and knowledge about watches with others. Nathan, our director of watchmaking, put together a series of articles entitled “From the Bench” to give you insight into how your watch works, how to use it, how to fix it, and everything in between. He tackles the big questions like whether you can overwind your watch (link here), what exactly it means to regulate your watch (link to part 1 and part 2), and how to properly size your bracelet (link here). He also published a couple articles on what happens to your watch when you send it in for a full service (link to part 1, part 2, part 3 and part 4). Check all of Nathan’s interesting and informative pieces below!

A Humboldt GMT with some Swag

Image of dark black watch with green seconds hand

February saw the release of one of our coolest brand collaborations to date. We partnered with fellow Chicago company SWAG Golf on a special edition version of our Humboldt GMT. The watch was designed as part of SWAG’s exclusive 2023 Super Bowl event that included 36 holes of golf, a three-night stay at the MGM Grand, a Super Bowl viewing party, a putting contest, and last but not least, the blacked-out Humboldt GMT SWAG edition. In contrast to our signature orange seconds hand and leather stitching, this watch featured SWAG’s neon yellow which really made this one pop! Check it out here.

We’re always open to brand and organization collaborations! Whether it be SWAG Golf, Wilson Sporting Goods, or the National Association of Olmsted Parks, we love working on designing and creating unique watches that tell your story. If you or someone you know is interested in creating a unique watch for their company or organization, send us an email, and let’s get the ball rolling! Click here for some inspiration.


The Beauty of Symmetry

The Olmsted field watch has been a staple of the Oak & Oscar collection since its launch in 2019. But a select group of watch enthusiasts yearn for symmetry. That’s why we launched a no-date version of the Olmsted in April. As always, we pride ourselves on doing things the right way; we never take any shortcuts. So there’s no phantom date jump or crown position on this watch. Whether your preference is date or no-date, we’ve got something for everyone!

Green Dial Olmsted Raffled for Charity

We believe that community is important at Oak & Oscar. From donating a portion of every purchase to One Tail at a Time to participating in various charity events, we like to give back in whatever ways we can. In May, a green no-date Olmsted was raffled off to benefit the Alexandria-Fairfax Alumni Chapter Kappa Scholarship Endowment Fund. This incredible organization monitors scholars throughout their college years to provide mentorship, career counseling, job placement assistance, and encouragement.

Founder Recognized in WatchPro Hot 100

Portrait of Chase sitting on couch with bourbon.

In June, our fearless leader, Chase, was recognized as part of WatchPro’s Hot 100 list. “The WatchPro Hot 100 celebrates the achievements and efforts of individuals in the watch industry who work tirelessly to improve their organization and the industry,” wrote title sponsor Tirath Kamdar, GM of Global Luxury at eBay. “It recognizes key names amongst the vast landscape of brands, retailers, services, marketplaces, and platforms.”

The feature charts Chase’s trajectory from corporate real estate consultant to watch company founder. And he’s featured alongside industry luminaries, including Eric Wind, Gabe Reilly & Asher Rapkin, Ariel Adams, and Roger Ruegger, among others. Check out the story here!

The Olmsted EXP-01

Watch on it's side. Case is bronze in color, dial is green.

Despite being in the watch game for close to 10 years now, we’ve never lost our sense of wonder at these mechanical machines. We like to think of our workshop as a kind of laboratory where we test out ideas just to see what would happen. As we like to say, Make No Little Plans. So in preparation for the Chicago edition of the WindUp Watch Fair in July, we put our lab coats on and thought up something pretty cool!

We wondered what would happen if we got stainless steel piping hot. So we got a kiln, and our director of watchmaking fired up a few Olmsted cases. The results were better than we could have ever hoped. What we created has the look of bronze, but it’s something that’ll patina in its own unique fashion.

The five pieces we made for WindUp sold out quickly, but the EXP-01 marked the start of a new series in which we plan to explore new techniques to keep pushing the world of horology forward. So there’s more where that came from!

We Welcomed a New Operations Manager

Image of Greg standing in front of brick wall with sunglasses and beard.

Another crazy thing happened in July. We welcomed our new operations manager, Greg Trotter (that’s me!), to the team. As it happened, my first week on the job was the same week as the Chicago WindUp. Talk about a trial by fire! The week was a whirlwind, but it gave me a chance to learn a lot about Oak & Oscar very quickly, meet some of our wonderful Owners, and to introduce some newcomers to the things I love about the brand. Check out more of my story here.

Built to Discover

Image of a group of guys in front of a field in Wisconsin

In August, we had a wonderful opportunity to take 14 Owners up to Wisconsin’s Driftless Area for a weekend of fly fishing, farm-to-table cuisine, coffee tasting, and good conversation. We stayed at the Red Clover Ranch, a beautiful 79-acre property in Soldiers Grove, Wisconsin. Fly fishing guides and gear were supplied by the Driftless Angler who made the experience memorable for both novices and experienced fishermen alike. We dined at the Driftless Cafe, a Michelin-quality restaurant tucked away in the quaint village of downtown Viroqua. And we had the unique opportunity to take a tour of Wonderstate Coffee Roastery and taste all the varieties of coffee they produce. Needless to say, the weekend was an incredible experience, and we can’t wait to go on some more adventurous journeys with our Owners. Plans are in the works for some upcoming trips, so keep an eye out!

The Humboldt GMT Titanium

In October, just before the flagship NYC WindUp event, we launched a titanium version of our Humboldt GMT. The watch is 20% lighter than its stainless steel predecessor, and the release gave us the opportunity to introduce a couple other new features. The Humboldt GMT Ti marks the first green dial in our Humboldt lineup. We also unveiled our new rubber strap that’s gotten rave reviews so far. We’re quite proud of this piece! Reviews of the watch have been featured in the likes of Worn & Wound and Fratello. Check those articles out here.

2023 Annual Owners Weekend

Guys sitting at dinner table

When you purchase an Oak & Oscar, you’re not just purchasing a watch, you’re joining a community. Our Owners are important to us, and we like to take every opportunity to show our appreciation. For this year’s annual Owners event, we hosted a private ticketed dinner at Half Acre, one of Chicago’s oldest and best craft breweries. We threw a huge celebration at our HQ the following night with food catered from Calo Ristorante, music, good conversation, and plenty of Old Fashioned cocktails. We saw everyone off with an F1/Bears watch party brunch at the Village Tap on Sunday. Take a look at some photos from this spectacular event here.

Owners Stories

Image of Alaska from an airplane

We clearly take pride in our Owners here at Oak & Oscar, and we like to highlight the incredibly interesting stories of the great folks that support us. We featured some amazing Owners stories this year. Photographer Dave F. gave us some insight into what it’s like to be a fishing photographer. Dave H. shared with us his amazing island situated just outside the Boundary Waters Canoe Area of northern Minnesota. And Alaskan fly fishing guide Nate G. gave us the rundown on living off the grid and the relentless mosquitoes that are a fact of life during summers in Alaska. We always say that our watches are built to discover, and these individuals really embody that spirit.

The Watch Table

Chase and Dan sitting at a table talking, with watches and cameras in front of them

Obviously, we love to talk watches. We’ve featured some amazing collectors on our Watch Table series this year. We saw everything from a platinum Tank to a custom Simpsons watch and some unique Leica-branded watches of unknown provenance. Click the link below to see these amazing pieces and hear the stories that make them so special.

Olmsted FEW Limited Edition

Watch with light red, deep salmon color dial sitting on top of bourbon bottle

To close things out this year, we released a collaboration a long time in the making. We partnered with our good friends at FEW Spirits on a limited edition timepiece with some really cool features! Chase has had the vision for this watch since before the Burnham was launched in 2015. So it’s truly special to finally see it in the metal.

Developing this timepiece allowed us to marry two of our favorite things: watches and bourbon. Using our classic Olmsted case, we made a watch that captured the spirit of both FEW and Oak & Oscar. The dial is a new one for us. Taking our cue from FEW’s well-known color palette, we produced a deep salmon dial that pairs wonderfully with the Horween leather strap on which the watch is presented. Those who purchased the watch were gifted a bottle of FEW’s Bottled in Bond bourbon to sip while staring at their wrists.

The feature that we’re perhaps the most excited about is visible through the sapphire caseback. That bottle of bourbon that came with the watch? We got to select the barrel ourselves on a trip to FEW’s distillery. To make the watch extra special, we tasked a local woodworker with breaking down the barrel and fashioning wooden disks that were placed in the caseback and engraved with FEW’s and Oak & Oscar’s company mottos. We’re super proud of this watch and couldn’t think of a better way to close out an amazing year.

We’re looking forward to 2024, and we can’t wait to see what it has in store!