Like we said, you’re spoiled for choice in the sub-$10,000 category: Rolexes such as Datejusts, Explorers, and Explorer IIs; Omegas such Speedmasters, Seamasters, and numerous others; all manner of funky chronographs; and solid gold dress watches galore from the likes of IWC, Vacheron Constantin, and Audemars Piguet…even Patek, if you really know what to look for. There are a few categories you won’t be able to touch for under $10k: minute repeaters, tourbillons, most annual or perpetual calendars, etc. But these ludicrously complicated watches cost tens of thousands for a reason, part of which is that they’re notoriously difficult to design and build. So if you want something like that, be prepared to shell out accordingly.

Unless you’ve been doing this for years and have bought and sold a ton of watches — and are prepared to pay handsomely for service in the vent that you buy a timepiece with a dud movement — we recommend that you do your shopping with a professional vintage dealer such as HODINKEE, Analog:Shift, Eric Wind, or Tropical Watch. While bargains can certainly be had on places such as eBay, shopping this way requires a lot of education: one has to know the characteristics that make a watch worth (or not worth) the money being asked by the seller, as well as what might actually be a steal, rather than a scam. So do your research carefully, and when in doubt, ask a pro. (Or better yet — buy from a pro.)

Yup, we realize that these things were like $2,500 not even five years ago. But times change, and prices rise — especially Rolex prices. So count your blessings that you can nab such a great, timeless model for around $5K, because truly, this is a hell of a watch for the money. When folks picture a Datejust, they’re often picturing a four-digit reference such as the fluted-bezel 1601 or the engine-turned 1603. (The former’s bezel is white gold, the latter’s is steel.) Perfectly sized at 36mm, paired to the iconic Jubilee bracelet, and powered by an automatic, in-house caliber from Rolex, the DJ is one of the most well known watches in the world — and for good reason. Strap one on before these things head north of $10K…there’s a good chance they will one day soon.

We will extoll the virtues of this slim dress watch ‘til the proverbial cows come home, and for good reason: The Albert Pellaton-designed Caliber 89 is widely agreed upon to be one of the best hand-wound movements ever constructed. Dating to the late 1940s, it powered the famous military-issued Mark XI from IWC and later, gold, steel, and (rarely) platinum-cased dress watches from the same brand. These dress watches are fairly readily available on the secondary market for under $5,000, even with solid gold cases. Just be sure to look for a correct dial, as many have been refinished over the years, which diminishes the value of the watch. (Be especially way of redials in steel versions, which constituted a smaller portion of the overall Caliber 89 production.)

There are 1,000 ways to buy a Speedy — or so it would seem — but it’s tough to argue with the value proposition inherent in the 1990s-era reference 3570.50. Housed within the classic, 42mm “twisted lug” Speedmaster case, these beauties feature handwound Caliber 861 movements, tritium dials and the Hesalite crystals that collectors love. With their closed casebacks and matching steel bracelets, these are true tool watches through and through — though to be fair, this is a watch that looks just as good (and works just as well) on any manner of factory or aftermarket straps, from fabric to leather to NATOs and more. Our advice? Nab one on a bracelet — it’ll be cheaper to throw it on a strap later rather than shell out for a bracelet down the road. 

While 1980s/early-1990s Rolex Submariner crossed the $10,000 threshold some years back, Subs from sister brand Tudor can still be had for between $5,000-$10,000. Tudor was set up as a less expensive alternative to Rolex and, as such, originally used off-the-shelf Swiss movements from the likes of Fleurier and ETA. These days, you can nab a 5-digit Tudor Sub — which uses Rolex hardware and an ETA movement — from the mid-‘80s/early-90s for well under 10k. These watches pair the best in vintage specs (such as Hesalite crystals and folded-link bracelets) with contemporary proportions and robustness. Find a good one on an Oyster bracelet, have it checked for water resistance and then take it SCUBA diving. That’s what they’re for!

When you picture a Tank, this is likely the watch that you’re picturing: a hand-wound Tank Louis in yellow gold. And though you can pick up a great hand-wound or quartz Tank from the 1970s or 1980s for under $3,000, we highly recommend the Tank Louis at roughly $6.5K — these superbly stylish dress watches recall a century of consistent design and look fabulous on men and women alike. Look for one whose case and classic Roman numeral dial are in good condition, and check that the small, hand-wound movement (get one with a hand-wound movement!) has been serviced. Then, go to town, especially if you have a black-tie event on the docket. That’s where these watches truly shine.

Dating to the mid-1950s, the Navitimer is perhaps the ultimate pilot’s watch, having been in production for over 70 years. With its multiple timing scales and slide rule bezel, this was a true “tool watch” in the original sense, designed so that pilots could make on-the-fly computations relating to navigation, fuel consumption, and more. Today, there are more Navitimer models available than one can shake a stick at, but we personally love the classic reference 806 for its stark, utilitarian beauty, its oversized (but not too oversized) case, its lasting design and its undeniable swagger. If you can find one with an AOPA (Aircraft Owners and Pilots Association) dial, then all the better — this is who these watches were truly made for.

Though Rolex’s GMT-Master is certainly the most well known travel watch, it’s by no means the only option. Back in the 1960s and ‘70s, Swiss firm Zodiac — which is now under the Fossil Group umbrella — made some of the coolest tool watches known to man. The Aerospace GMT, which has seen several modern iterations released in recent years, was one such watch: Though small by today’s standards at just 35mm, its simple functionality, good looks, useful dual-time complication and folded-link steel bracelet made for a tremendous design. (Indeed, Zodiac watches were offered in military post exchanges overseas, and American servicemen are known to have worn them in conflicts such as the Vietnam War.) Today, they can be had for under $3,000.

While vintage designs such as the A385 and A386 featuring the famous, automatic El Primero movement have crossed the $10,000 threshold lately, other hand-wound, slim, dressier chronographs from the Le Locle-based maison are much more affordable — and largely overlooked. Indeed, these are some of the best of the “dressy chronograph” category, with some even featuring solid gold cases. Powered by thin, mechanical calibers from the likes of Excelsior Park and Martel, these ~37.5mm watches pair beautifully with vintage-style leather straps, and work well for everyday wear or with a suit and tie. Though they can be had for a bargain on eBay and the like, we recommend paying a premium for one from a proper dealer, as servicing vintage chronograph movements can be expensive.

Though you perhaps can’t get into a perpetual calendar, tourbillon or minute repeater for under $10,000, you can most certainly find your way into a hell of a complicated watch via the likes of the awesome Yema Yachtingraf. This unique regatta timer was available in several iterations through the 1960s and 1970s — and with several names on the dial, given the complexities of 20th-century watch distribution in different markets. But suffice it to say that this thing was truly a small, mechanical computer: Using its unique dial aperture, it’s possible to properly time a regatta countdown — or other event of your choice. Even if you don’t yacht, bro, there’s no denying that this hand-wound marvel is the type of timepiece that gets any collector’s heart racing. (Not to mention his yacht.) 

While contemporary iterations of the famed spelunker’s Explorer II will cost you well over 10 Gs, the undeniably (in our opinion) better proportioned reference 16570 can be had for between $7-10K. Available in black or white dials — the white being more expensive given that color’s rarity within the Rolex sports watch oeuvre — this 40mm tool watch is a true traveler’s timepiece in that the 24-hour hand can be set independently. Search for one with an Oyster bracelet and a tritium dial if possible; later models feature SuperLumiNova dials, which don’t develop that creamy color that we all (somewhat inexplicably) seem to love. This article was featured in the InsideHook newsletter. Sign up now.