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The Perfect 3-Watch Collection Under $5,000

December 22nd, 2020

Which watches would you choose?

What would you do if you were given $5000 and the only strings attached to it were that you had to build the perfect three-watch collection? How would you decide which watches to choose? But, more importantly, which watches would you choose? I’ve got a few ideas and I’ve put together two of my “perfect” three-watch collections for under $5000.

Some Ground Rules

Versatility is most important, though, as we’re limited to a three-watch collection. So, consider watches to be worn in multiple scenarios. A dress watch, sports watch, and an in-between everyday watch cover all the bases.

Since price is a factor as well, consider going pre-owned. A gently-used luxury watch from a reputable dealer will deliver serious bang for your buck.

Even with these considerations, it’s difficult to nail down just three watches. I did my best, though. Let’s check ’em out.


1. Seiko Spirit SARB033 – $800

3 watch collection under 5000

I’m starting off the first collection with the Seiko SARB033. This is my everyday watch here for this collection. Only available as pre-owned now because it is a discontinued model, with an average price of around $800. Seiko, of course, great brand history. The design is very simple. Great value for the price. And I specifically chose this one as my everyday watch because it is so incredibly versatile. At 38mm, it’s a great size for just about any wrist. It’s an automatic movement. It’s got a see-through case back and an absolutely gorgeous dial. Date window is very practical. Stainless steel bracelet. I love the mix of the polished and brushed steel throughout. It’s a beautiful watch that I think looks much richer than its price tag.

2. Tudor Heritage Black Bay 79230N – $3500

3 watch collection under 5000

For our sport watch, I’m going with the Tudor Heritage Black Bay 79230N, coming in at around $3500. This is a much-loved and very highly-regarded watch. 41mm stainless steel case. Screw down crown. 200m of water resistance. Beautiful matte black dial with rose gold-plated indicies and hands. It’s got a uni-directional diving bezel with the 60-minute track printed on the aluminum insert. The automatic movement is the in-house caliber MT5602. Variety of bracelet options, including a steel riveted bracelet, a leather strap with a folding clasp, or a NATO strap. And that really is one of the best parts about a dive watch like this in that you can really increase its versatility and give it an entirely new look just by changing the bracelet.

3. Vintage Omega Seamaster – $700

3 watch collection under 5000

For our dress watch in this collection, I decided to go vintage and I chose a vintage Omega Seamaster, which comes in at around $700 though they can definitely be found for less than that. I like this one as a dress watch because of its elegance, because of its simplicity, and because of its size. In the vintage Seamaster realm you’re looking at about a 35 or 36mm case. I love a smaller case size for a dressier watch–I think it gives it a real sense of old school understatement and elegance. And I think a vintage piece when we’re talking about dressed up looks or even a formal look is a perfect match.


1. Hamilton Khaki Field Mechanical – $500

3 watch collection under 5000

Starting off with the everyday watch and for this one I’m choosing the Hamilton Khaki Field Mechanical–this is the H69439931–coming in at $500. A little bit more rugged of an everyday pick compared the Seiko SARB, but this collection I’ve kind of geared more towards an overall casual feel, though we do have a very classic dress watch pick that you’ll want to stick around for. This watch though, is 38mm–again, a very versatile size. It’s got that great military look. You’ll see it mostly on a fabric strap though you can definitely add a leather strap if you like. One thing to know about this one is that it is not an automatic movement, which means you’re going to have to wind it, but for me, I love the connection that actually winding the watch creates between you and the watch itself.

2. Omega Speedmaster Reduced – $2500

3 watch collection under 5000

For our sport watch here, I’m going with the Omega Speedmaster Reduced–3510.50–coming in at $2500 though you CAN find them for less. Great classic chronograph, unmistakable looks, and extremely versatile as it just looks amazing on so many different types of straps. It’s called “reduced” because of the size. The typical Speedmaster Professional is going to be 42mm. Mine, the First Omega In Space is just under 40mm. And the Speedmaster Reduced is 38.5mm. Just something to be aware of. But if your wrist is on the smaller side and you do love the Speedmaster this is a great choice at an excellent price point.

3. Cartier Tank Solo – $2000

3 watch collection under 5000

The iconic Cartier Tank rounds out the second collection. And, what a way to finish! The watch is the epitome of elegance, and pairs just as well with a sports jacket and trousers as it does a tuxedo.  Now, this does put us right at that $5,000 limit, and it is a little a difficult to find this watch at the $2,000. However, you can do it if you know where and how to look.

Building on a Budget

Even with $5,000, there are any number of ways to slice this pie by three. You could dump the vast majority into a single item and clean up with some budget options. Or, you could spend exactly $1,333.33 on each and get lucky with the extra penny. The choice, ultimately, is up to you.

But, I’d like to hear from you. What would you choose for a three-watch collection with $5,000? Or, would you wear a watch with a tux?

Thanks for reading.

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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