Four Years On, This Boutique American Watch Brand Is Still Marching to the Beat of its Own Drum

Chicago-based Oak & Oscar is constantly innovating, delivering some of the finest watches to come from the microbrand movement.

We last spoke to Chase Fancher, the founder of Oak & Oscar, back in 2017. At the time, we noted that Fancher had led the brand on a steep climb in popularity after just two watches. “I hope I’m lucky enough to make another watch,” Fancher said at the time.

Now, two years later, he’s made not just one more watch, but four: the Jackson, a flyback chronograph, the Humboldt, a field watch with a 12-hour bezel, the Olmsted 38, an understated, slightly dressier piece, and the Ashland, a hunk of a watch inspired by baseball. Just like the ones before it, those watches have flown off shelves. We spoke with Fancher about that continued success, becoming an OG indie brand, and why not pleasing everyone is OK in his book.

The Jackson flyback chronograph; the Humbolt automatic with 12-hour bezel; the Olmstead automatic; the Ashland with special inning timer bezel.

Q: We’ve talked before about how you started Oak & Oscar. But I don’t think I’ve heard where your initial love of watches came from.
A: I’ve always loved watches. As a kid I had those cheap freestyle diver watches with velcro straps, the Casio calculator watch, the Ironman watches from Timex that you get at the checkout line. The idea that you could wear them in a pool, or doing something else, was fascinating.

It wasn’t until after college that I started getting into serious watches. I checked myself, and wouldn’t let myself go too deep, because I knew I’d go crazy. Once I got a good job, I let myself start a serious collection. And then of course I went in very deep.

Q: What was the first “serious” watch that you really obsessed over?
A: One of the first ones I lusted after for a while, was the Speedmaster, like a lot of folks. As well as the Tudor Black Bay, as well as Panerai.

Q: Do you have a type when it comes to watches?
A: Sure. There’s some diversity. But I’m drawn to orange accents, grays and navies, no surprise there. As well as watches that are well designed. I have a blue-dialed NOMOS World Timer that I love. Its beautiful because it’s slightly different.

I’m not the guy who collects a piece because of the specific movement references. I’m drawn to the watch itself. I need to fall in love with the watch every time I put it on.

Q: When it comes to orange, is there ever too much for you? Are you reaching for the DOXA Professional?
A: DOXA is a great brand. The orange dial is a really fun piece. It’s definitely not too much. A brand that throws an orange dial out there, something crazy, more power to them. Somebody out there is gonna love them. It gives people more choices.

It’s gonna rub people the right way or the wrong way. But actually I’m a huge supporter of that. [At Oak & Oscar] we don’t wanna do something that every single person loves, because that means it’s probably a little boring. For us, we would like to strike that line of someone being passionate about it because they love it, and then someone also disliking it. That’s OK.

“We don’t wanna do something that every single person loves, because that means it’s probably a little boring.”

Q: With indie brands, I’m always curious about the “Eureka!” moment, when you realized that things were going to work out as a watchmaker. Did you have that moment?
A: There’s been a lot of times when I’ve pinched myself and thought, is this really happening? When people come to the shop, and they take off whatever watch they’re wearing to put ours on. We have folks come in here and take off everything from a Seiko to FP Journe to Rolex to Ressence. Whenever that happens, I’m a little blown away. It’s a huge honor.

In terms of specific example, it was Eric Wind at Christie’s in New York. I was there to show off one of our recent releases to folks, and I happened to be there the same day as a big watch auction. So I went there, and I was hanging around and talking to watch guys I knew, and they introduced me to Eric. I’d seen his photo before. He said, “Oh, yeah, Chase, from Oak & Oscar! I really like what you’re doing.” So here I am at this Christie’s watch auction where people are dropping lots of cash on really cool watches, and one of the VPs of the auction recognizes me and compliments me.

Q: Oak & Oscar is known for its sandwich dials. What is it about the sandwich dial that grabs people?
A: What I love about the sandwich dial — and I’ll say that a dial can be interesting regardless, our Jackson has raised indices—is the depth. It gives an idea of the architecture that’s going on there. It’s not something you see every day. And it’s an extra, added detail bonus. People tell me they enjoy the visual aesthetic of it. And the fact that it’s an extra design detail that isn’t just a printed dial. Don’t get me wrong — printed dials can be done beautifully. They are far easier to make. Sandwich dials are remarkably complicated to do right.

Q: You’ve been going at this for almost five years now. What’s changed about the indie watch industry during that time?
A: I think more people are aware that smaller brands like us exist. It’s become a bit of a thing. The problem with that is there are so many bad apples out there. Bad examples of small brands who take people’s money and give them a watch that’s not worth it. That happens in any industry. What’s great is you have the ability for the good brands to rise to the top. That’s something that’s certainly changed over the past several years in this industry. The brands that are good, high-quality, based on their price point, they’re hopefully gonna stick around.

Q: Something I hear quite a bit from indie watch owners is that they get loads of emails, and lots of those emails are happy ones, and some are unhappy ones. I’m curious, since you mentioned earlier that you don’t want everyone to necessarily love your watches: when you get one of those bad emails, and someone doesn’t like one of your new watches, for whatever reason, how do you deal with that? Is it personal?
A: Truth is, it is without a doubt personal. John [Hatherly, Oak & Oscar’s creative director] and I put our personal preferences and style into these watches. It’s very important to us that they reflect our design. That to us is very valuable. We know that not everyone likes everyone’s personal design. And that’s totally OK. We have our own personal style. This is what an Oak and Oscar looks like. This is how it feels. And of course we can vary off that — add different characteristics, design traits, styles — and it still is putting out our same Oak and Oscar message. We’re not out there to make the same watch that everyone’s already seen from other brands.

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