You can walk into any store and get a perfectly decent watch, a good one even, for $500. But if you show a little imagination, you can find a much sexier vintage watch on eBay that will make a much bigger impression.

My go to watch is a Girard Perregeux Gyromatic from the 1960s. It’s simple, elegant, it comes with a back story and it’s a great example of getting the details right. I’ve had more comments on that watch than any modern one I’ve ever owned.

You see we all know that girls notice the details, but a lot of guys get it badly wrong by buying a big, brash and tasteless watch that only appeals to other guys. We do the same with cars.

Business Watches Can Be Brasher

That can be worth something in business and we’ll go into bigger budget boardroom specials another day. But even in business, the right budget vintage watch can be a talking point that helps win people over.

You don’t need to go out and buy a massive Rolex, or the latest Tag Heuer. You can find vintage watches for sale online that blow them all out the water.

You can spend a fraction of the money and show through your choices in life that you’re a connoisseur, rather than a simple consumer. You can show that you appreciate the classier things in life and you can demonstrate understated elegance, rather than talking about it.

You can even go cheaper. Read my guide to $200 vintage watches that will raise your fashion game here.

Don’t Fancy eBay? We Have An Answer

You might not trust eBay and that’s understandable with highly complicated stuff like this. So if you just want a clean example of a vintage watch and you’re prepared to pay a little more, the try the International Vintage Watch Company.

Show, Don’t Tell, Your Class And Taste

Always show, don’t tell. Your watch is just one of the ways you can do it.

The PUA community often recommends peacocking, by the way, standing out with oddball clothes and jewelry. This is not the same thing. It is not flaunting unusual curiosities in a girl’s face. It’s simply a case of giving your details a narrative and making a conscious decision to make more interesting choices.

Peacocking theory has almost certainly made otherwise sane men use a pocket watch on a chain as well. Don’t do that, it makes you look like a tool…

Beware that vintage watches can become an unhealthy addiction, so don’t go nuts. A couple of well-chosen watches will cover you for every eventuality and I really just wear the one. Also, if you go the eBay route, be wary of fakes and do your homework on the watch and the vendor.

So what are the best vintage watches for under $500?

1. Tag Heuer 2000 Series

Year: 1982-90

Price: $300-$700

Check a selection of Tag Heuer 2000 series watches on eBay right now.

The Tag Heuer 2000 is the watch that took this Swiss company into the mainstream and is pretty much the founding father of the company’s modern design philosophy.

It came in a variety of styles, but if you can find one of the early stainless steel watches with a flat black bezel and dial, with a monochrome logo, in your budget then go for it. Later watches came with a raised stainless steel bezel and this is the one that became the watch’s calling card. It survived until 2005, which means there are a lot of these classic vintage watches for sale online.

eBay is full of fake Tag Heuers, so buy at your peril, but this page has some pretty solid descriptions and photos of the various models:

Tag Heuer 2000 history and models

Get a good one and you’ll be shocked at the value. It’s one of the cheapest vintage watches on this list and you could pick one up for the price of a new Fossil if you look hard enough. Spend a few more bucks and get a good one, though, and this could be just as impressive as the modern day beasts that cost ten times more.

Watch guys will love it, casual observers will think it has to be worth serious money and it you’ll appreciate a true piece of engineering every time you put it on your wrist.

2. Jaeger LeCoultre Memovox

Best year: 1950-65

Price: $500-$7000

Check a selection of Jaeger LeCoultre Memovox watches on eBay now.

This company will sell you a vintage watch for millions of dollars, with the Jaeger LeCoultre Hybris Mechanica Grande Sonnerie weighing in at $2.5 million. For just $500, though, you can buy a 1950s special that arguably looks just as good.

It has the brand cache, so gold diggers that know their names will still think it cost big money and others will approve of the clean lines and antique look. You can talk to them about the mechanical alarm, which was a big deal when this watch launched, or you can just tell them that you found it in a back street market in Paris, Milan or New York and you had to have it.

Either way, this watch will score big points and punch well beyond its price range.

In 1956 it became the world’s first self-winding alarm watch, which makes that era particularly collectible. Then in 1965 a Memovox Polaris came with a triple back to improve sound transmission underwater.

Be careful with the collector’s watches, though, you can pay dearly in terms of price or condition for the most highly-prized watches. You just don’t need them if you want a stylish piece that you’ll actually wear, so do your research and focus on a cheaper model that still looks the part.

Stay away from the insane eBay bidding wars that can easily kick off with the special variants of this kind of watch. Just get one you’ll enjoy and leave the details to the anoraks.

Now we have to be honest, the Memovox doesn’t come up all that often in this price range and Jaeger LeCoultre makes some seriously stunning timepieces that you might like more.

Most of them cost thousands, but you can find them for around $500.

Have a look here for more vintage Jaeger LeCoultre watches that are roughly in the price range.

3. Omega Seamaster

Best year: 1948-1960

Price: $460-$10,000

Check a selection of Omega Seamaster watches on eBay now.

The Omega Seamaster is one of the most revered watches in this price bracket, in part because they can cost so much more. You can spend more than $10,000 on the ‘right’ Seamaster, but you just don’t need to.

James Bond, Jeremy Clarkson, Joe Biden and Adam Savage have all worn one and that means that the watch has been reinvented a number of times in different styles. So it comes with a series of different price tags.

The chunky diver’s watch with the stainless steel strap and black, blue or silver dial are the most sought after. For the full effect, look out for orange accents on the dial, too. That’s the one you want, if you can find one in your price range.

It’s waterproof to 1200 meters, has a real mechanical feel in the hand and a weight that will rival anything on the market these days.

You can find Omega Seamaster dress watches for relative pennies, but they’re a perversion of the basic concept. If you can live with that, knock yourself out and pick up a watch for $50.

eBay is absolutely awash with them, but you might have to root around and lose a few before you get one for this budget. It’s worth the effort.

4. Girard Perregeux Gyromatic

Best years: 1957-65

Price: $300-$1000

Check a selection of Girard Perregaux Gyromatic watches for sale on eBay

This is my go-to watch now and the 1960s design combines well with a modern metal strap, although purists will tell you to go with a leather one.

My watch belonged to my grandfather and it still doesn’t miss a beat. It kicks into life every time when I put it on, thanks the gyromatic auto wind system that relies on a simple weight inside the watch that starts the movement.

Mine has 39 jewels, while the earlier models came with 17 and actually are more desirable for collectors. That means they tend to be more expensive, so if you’re just looking for an elegant watch then steer clear of the highly-prized models and just get a good example of a later watch.

The Gyromatic was a popular watch and you’ll find all manner of different styles spanning decades of production. So go for the one you like and wear it with pride. It’s a detail that makes a big difference.

This is the cleanest, simplest watch I have ever owned and yet it gets the most comments. I love the combination of the old face and modern strap, even though the irregular shape of the Gyromatic means it doesn’t quite fit the curve of the buttress. It’s all part of the narrative and it catches the eye without being a dick about it.

5. Hamilton Brock 14K Gold

Best years: 1947-60

Price: $200-$800

Check a selection of Hamilton Brock 14K watches for sale on eBay now.

Hamilton represents everything that was great about the old world of American engineering and the company dates back to 1892. It is still going strong and they have a stellar modern range, but there’s something about this chunky, squared off 1947 special that I just love.

The solid gold numbers are clearly placed on the dial and there’s just enough character and design to catch the eye. It’s retro, cutting edge and luxurious all in one striking package and it could look stunning mated to a high-end leather strap or even something modern and metallic.

There are enough of these watches about that you can take a punt on eBay and potentially pick one up for a few hundred dollars, too.

Smart American salesman could use this great time in US precision engineering as a pitch on its own. For businessmen it’s a great talking point and this is one of those watches that would be a perfect power meeting accessory.

6. Tissot Seastar Automatic

Best years: 1965-70

Price: $80-$1000+

Check a selection of Tissot Seastar Automatic watches for sale on eBay.

The heavy lump of a vintage diver’s watch is one of the best you can find, but look at the Seastar dress watches for the real bargains.

You can pick one up for as little as $30 and you’ll get Swiss engineering and a serious brand for your money. A new Seastar, and they are still on sale, will cost from $700.

Tissot has been around since 1853 and the Swiss company is on the fringes of ‘luxury’, but it still carries a certain level of brand cache. The vintage watches are solid hunks of engineering with a glass smooth movement that even watch snobs will grudgingly admit is as good as anything else out there.

7. Grand Seiko Hi Beat

Best years: 1968-75

Price: $400-$7000+

Check a selection of Grand Seiko Hi Beat watches for sale on eBay now.

This one is a left-field option, but if there’s a real men’s vintage watch nerd in your life then they could have a 50K Panerai on his wrist and they’ll still dribble all over your Grand Seiko. If you let them…

This was a halo watch for the Japanese firm and while others might recommend the more common King Seiko, the Grand Seiko Hi Beat is the one you really want. At the time Seiko had two in-house design teams competing with each other, Grand and King. In most real experts’ opinion, Grand won the battle and you’ll even hear the hardcore fans claiming the Grand Seikos have better build quality than all but the best Rolex watches.

It’s a simple vintage dress watch and there’s really not much more to say. It doesn’t stand out like some of the other watches here, but it is revered, beautifully simple and easy to find within the budget.

8. Bulova Snorkel Dive Watch 666

Best years: 1963-68

Price: $300-500

Check a selection of Bulova Snorkel Dive Watch 666 watches for sale on eBay now.

This 40” vintage dive watch isn’t as big and brash as the modern equivalent, although the retro colors are a challenge, but it sits nicely on the wrist and its Americcan built, too, although Bulova used to be an American-Swiss company it is now 100% Murican, although Citizen owns the title deeds.

You can pick them up for $300 and up and most of them come with a canvas strap. Personally, I’d replace that and turn this old and elegant vintage divers’ watch into a real show stopper with a polished metal strap or a seriously thick leather band.

Mount it right and the Bulova is a match for anything on the market in terms of pure aesthetics and watch enthusiasts will give you instant respect.

Jacques Cousteau had a Bulova alongside his Rolex Submariner, which should tell you all you need to know about its abilities as a dive watch.

That’s what kind of vintage watch is for sale online for less than $500, but we can find something even cheaper for you too.

Check out our guide to $200 vintage watches that will raise your fashion game.

And when you’re done there, see the cheapest vintage watches that you can buy online for less than $100.