Fratello Favorites: The Best Vintage Watches Under €5K — Thomas’s Picks From Omega, Rolex, And Grand Seiko

Welcome to another series of Fratello Favorites! Our writers get another chance to share their favorite watches within a certain segment. This time, we are tackling vintage watches under €5K. I am the lucky first to outline what I think are the best vintage watches in the price range and why. Over the coming weeks, you will see my fellow Fratello teammates share their picks.

Now, we did not get any guidelines other than “vintage” and “under €5K”. However, I am adding a third condition of my own. I will only pick watches that are easy to buy and own. That means you will find plenty of information on them to make an informed choice, and you will not struggle to get them serviced or source parts for them. These should make for a nice and easy transition into vintage watches. So, without further ado, let’s get into it!

The best vintage watches under €5K: Rolex Datejust

You did not expect any other first pick from me, did you? I wrote the book The Vintage Rolex Datejust Buyer’s & Collector’s Guide in 2021, which was a major personal and professional milestone. Please don’t accuse me of plugging; I no longer sell the book, and there will not be a second edition. Still, the Rolex Datejust has a very special place in my heart thanks to the entire project.

That said, a vintage Rolex Datejust should be mentioned as one of the best vintage watches under €5K regardless. You can now find great ones in the €4K–5K range, which buys you an absolute classic. From the fluted bezel to the Jubilee bracelet and the divisive Cyclops crystal, it is one of the most iconic watches of all time.

I usually advise to look at the 16xx, 16xxx, and 162xx generations. These offer all the vintage charm you could want, paired with reliability and easy serviceability. The first gives you a pie-pan dial, the second a quickset date, and the last a sapphire crystal. Add to this the infinite variety within each generation, and there is surely a vintage Rolex Datejust to suit your taste.

A non-diver Omega Seamaster

Now, what if you are on a slightly tighter budget but you like the vibe? Well, a 1950s/1960s Omega Seamaster offers a great alternative. Reference 166.010, for instance, is a fantastic-looking everyday watch you can find under €2K any day. Get it on the jangly beads-of-rice bracelet for the full vintage experience.

Again, there are infinite options to choose from here. I am particularly speaking of the non-diver models. A vintage Seamaster 300 will surely be out of reach for our budget. However, watches like the pictured Seamaster ref. 2846 certainly apply as some of the best vintage watches under €5K. I have two in radically different guises. By today’s standards, these look and feel more like dress watches than sports watches. Still, they have plenty of wrist presence and a tough build for their age.

A Seamaster ref. 166.010 — Image: Amsterdam Watch Company

You can find variations in steel, gold, or gold-capped cases. Dials come in many styles, with different indexes and variations of crosshair prints. It pays to do your homework on the calibers as some are easier to get serviced than others. Still, roughly €1,000 buys you a fantastic specimen that will surely bring joy for many years to come.

An original Grand Seiko 44GS

Grand Seiko 44GS

My third pick for the best vintage watches under €5K is the Grand Seiko 44GS. The 44GS arguably holds the throne as Grand Seiko’s most important watch. Launched in 1967, it is the pinnacle of Taro Tanaka’s Grammar of Design. Imagine how futuristic it must have looked then with its stern, flat surfaces. Actually, it still looks rather fresh today. This is a truly timeless watch, for lack of a better word.

Granted, a Grand Seiko 44GS is significantly harder to source than my other two candidates for the best vintage watches under €5K. You will need to do your homework. But hey, that’s half the fun! You will learn about neat stuff, like the Daini Seikosha factory logo on the dial and the 4420-series calibers inside.

The one pictured here belongs to my beloved colleague Mike, who, I am sure, is livid with me now for picking it ahead of him. If you want to learn more about this beautiful watch, be sure to read his article on it.

The best vintage watches under €5K — Closing thoughts

There you have it — my three picks for the best vintage watches under €5K. Of course, these are only a very non-representative tip of a massive iceberg. I guess they show my love of mid-century GADA (go anywhere, do anything) watches quite clearly too!

I’m looking forward to my colleagues’ picks as they will surely broaden the scope significantly. I can foresee Nacho presenting some fantastic dive watches. Mike will surely bring your attention to some chronographs. I wouldn’t be surprised to see some stuff from the 1980s and ’90s from others as well.

Still, I am happy with my three picks here. These three categories offer tremendous value, variety, and historic significance. They also represent my style to a tee, which is always the goal with our Fratello Favorites articles.

What would be your picks for the best vintage watches under €5K? Let us know in the comments section below!