“When I was a freshman in high school I wasn’t all that interested in history,” says Jason Ruedas, the owner of Rue Vintage, a small, online shop that sells vintage chronographs, many through Instagram. But in his bio, Ruedas refers to himself as “a wannabe historian,” and the watches on his website are listed with as much information as he can scrounge up. “Eventually you grow fond of it when you’re an adult, and you’re surrounded with all these old things, and you have to sell it and explain to someone why it’s rare and why they should buy it.”

Ruedas’s business is not the result of a long-term love affair with watches; it’s merely a logical progression of a lifetime selling things. As Ruedas tells it, when he came to New York from the Philippines in the mid-1990s, he just needed to make ends meet. That started with selling bootleg concert tapes, but it eventually progressed into the practice of retail arbitrage: buying things at a discount in-store then flipping them for a profit online.

“I got this from my mom, because back when I was a kid, she would sell jewelry,” he says. “I remember being dragged into jewelry stores and pawn shops, and she would buy jewelry and flip it to our neighbors, to people she knew she could sell to.”

In addition to selling watches, Ruedas makes a living selling vintage and hard-to find video games and memorobilia. This is just a snapshot of his impressive collection. Photo by Jason Ruedas

Eventually, Ruedas settled into to a steady gig finding and selling rare and hard-to-find video games and gaming gear, but he soon developed an interest in watches. At first, it was mostly the kind of timepieces watch nerds cut their teeth on: mechanical Seikos, Orients, even some Fossils. But Ruedas soon fell in love with the Hamilton Chrono-Matic, one of the first chronograph watches to use automatic winding. “I thought this watch is really cool, it’s small… about 36mm, so these were like perfect on my wrist. They looked great, and they were still sort of affordable at the time.”

According to Ruedas, the Hamilton proved hard to track down, as Chrono-Matics that went up for sale were quickly acquired. Seeing their prices rise throughout this game of cat and mouse, Ruedas realized the potential in selling watches like the Hamilton Chrono-Matic.

“I was like this is it, then, I should do this,” he says. “I had to learn everything. I had to learn movements; I had to make sure everything was not necessarily pristine, but correct.” With the help of a jeweler and watch repair shop in New Jersey, Ruedas “rescues” many old chronographs he finds for sale and flips them via Instagram and his online store.

The watches you’ll see on Rue Watches are not the stereotypical Heuers and Omegas. Instead, he has a predilection for lesser-known brands and chronographs from the mid-20th century. “I want something nobody else has,” he says. “Everyone has Speedsters, and everyone has Rolexes, but nobody has old brands like Vulcain or Lip. They too have history, but it’s sort of lost between the people who worked there. It’s all lost in the online message boards; you have to dig.” With the help of forums like WatchUSeek and other Instagrammers, Ruedas pieces together tidbits on the watches he finds.

That’s precicely what’s so appealing about Ruedas’ collection and most of these watches in general — they’re a far cry from what you’ll usually see on other peoples’ wrists. And while some of Rue’s watches are priced relatively high due to their rarity, they still undercut the price of many more well-known chronographs by thousands (though Ruedas notes they’re starting to catch on with collectors). With that in mind, we asked him for suggestions on three vintage chronograph brands to seek out now.

Hamilton

“I think Hamilton is still very affordable compared to Heuer and Breitling — all these other brands are skyrocketing so quickly. The chronographs, they’re special to me. Mainly, specifically, the two-register ones. It’s such a clean design and it’s very affordable and it looks like million bucks. And it’s not pretentiously big.”

Wakmann

“These are watches from the ’50s to the ’70s — [they’re] still very affordable and [there are] still plenty out there. These are beautiful watches, and they are one of the only companies who went so far on the triple dates. These are really collectable. I specifically like the Gigandet line because they’re a bit more rare and a bit more refined.”

Lip

“I really like Lip because a lot of [their] watches didn’t survive. The brand still exists now but it really isn’t the same. They really did design most of their dials from scratch.”