So after months of scrolling through eBay and Chrono24, you finally want to buy your first vintage timepiece. But where to begin? It’s wise not to jump right into the deep end by spending five figures on a vintage Rolex Explorer or Submariner; it’s easy to get duped when buying vintage, and you don’t want a beginner’s mistake to become an expensive beginner’s mistake.

A natural starting point is the hundreds of Omega Seamasters and Rolex Oyster Perpetuals you’ll find on secondary marketplaces everyday. These are accessible watches (often under $1,000 in the case of a vintage Seamaster) from the best known brands in watchmaking. But what if you want to dig a little deeper and find a real signature timepiece? A watch that defined its era, broke new ground, or just looks damn good. Happy hunting!

Here are some vintage watch recommendations in the $2,000–$6,000 range that will help you stand out from the crowd

Universal Geneve Polerouter

Some of the best vintage values can be found in extinct brand Universal Geneve. Our first stop is the Polerouter, designed by a 24-year-old Gerald Genta (of Royal Oak and Nautilus fame). Originally designed in honor of a flight over the North Pole in 1954, you can purchase a Polerouter knowing you own a unique, and little-known piece of watchmaking history. The gently curving lugs, ridged outer circle and crosshair make the watch easily distinguishable, but the 34mm diameter means it goes comfortably with anything. Additionally, even pristine examples of this watch won't run you more than a couple thousand dollars, so you can pocket some of that money and begin saving for your next purchase. While I'd love to suggest springing for a Universal Geneve Tri-Compax, I'm afraid you won't be able to find a good example at this price, and you'd be better serve finding a clean Polerouter instead.

Price: $1,000–$2,000

Grand Seiko

In the modern luxury space, Grand Seiko may offer more watch per dollar than any other luxury brand. The same may be said of its vintage timepieces. With parent company Epson Seiko recently announcing that Grand Seiko would begin to market itself as a standalone brand (dropping the Seiko name on its dials), and spinning off Grand Seiko USA into a separate entity, it’s clear that the company has high ambitions for its luxury brand to compete on a world stage. For vintage pieces, this means one thing: scoop them up while they’re still cheap(ish). The Grand Seiko Guy has done incredible work cataloging the history of Grand Seiko, and has also made his website a destination for purchasing vintage GS timepieces.

Price: $2,000 and up

Rolex Explorer Ref. 14270

Okay, $6,000 isn't going to get you a delicious Explorer 1016, but it might get you the subsequent Reference 14270, which replaced the 1016 in 1989. The 14270 updated the late 1016's matte dial with a glossy dial and white gold surrounds on the applied indices. The 14270 stayed true to the original Explorer's 36mm diameter, albeit with a new Caliber 3000 movement. And while a watch from 1989 might not sound like a true "vintage" piece yet, it is nearly 30 years old, and with Rolex's latest update to the Explorer reaching 39mm in diameter, it's now clear this is a design of the past, meaning our collective appreciation for it will only rise over time. Sure, you can get an old Oyster Perpetual for less, but don't you want a true Rolex sports watch? Or, for a true vintage Rolex in this price range, you can also check out an Air-King Ref. 5500. For more, read our history of the Rolex Explorer.

Price: $5,000–$6,000

IWC Dress Watch (with Caliber 89)

Powered by IWC’s famed Caliber 89, which was used to power IWC’s Mark XI until the 1970s, a vintage IWC dress watch is something that never goes out of style. Similar in form to more expensive Patek Phillipe Calatravas or Vacheron Constantin dress watches, this watch will have you looking like a serious collector without having to spend the money. IWC made these dress watches in gold and steel, and while you probably won’t find one with an untouched dial, they’re still worth picking up for the history alone.

Price: $2,000–$3,000

Longines Calatrava

This recommendation is similar to the IWC dress watch tip. For a fraction of the price of a Patek Calatrava, you can pick up a vintage timepiece from a Swiss brand with an even longer pedigree than Patek Phillipe. Their vintage dress watches are simple, elegant, and go with anything. And with what (in my opinion) is one of the best logos in watchdom, you can’t go wrong.

Price: $1,000–$2,000

Omega Speedmaster

You won’t be able to get the famed Moon watch, or even a pre-moon watch with Omega’s famed Caliber 321 for $6,000, but you can pick up a 1970s Speedmaster that looks a lot like one. And while you might be able to pick up a new Speedmaster Professional for a little more, isn’t one with some history just more fun?

Price: $3,000–$4,000

Breitling Navitimer

First produced by Breitling in 1952, the Navitmer is the quintessential pilots’ watch. It’s still a moderately priced vintage chronograph and worth picking up if your fancy yourself a pilot.

Price: $5,000–$6,000