I get asked this question a lot, and if I received a dollar every time someone asked me, maybe the article would be titled “if I could get any watch.” But alas, if I could only get one watch, what watch would it be? Well, it’s a good thing you ask as I have just the answer for you!

Before I share my choices though, it’d be appropriate to share my rationale for making them. To me, the one watch collection must possess the following characteristics:

  • It must be versatile – I wouldn’t have the option of having one watch for formal occasions and another for afternoons on the beach. So a watch must be versatile, in that it could be dressed up or down as it pertains to any particular occasion. For a single watch collection, versatility is key.
  • It must be from a watch brand/house – Sure you could get a watch from Michael Kors or Nixon, or even Diesel, but it must be stated that these blocks of metal aren’t true watches; they are simply fashion pieces. The watch brand/house therefore must be considered when purchasing a watch.
  • A watch must tell time but be timeless – Watches aren’t supposed to be about fashion and glamour; a beautiful watch will be stunning today and will be equally so 50 years from now. True watches are supposed to tell you the time and articulate that time beautifully. So absolutely no faux gold watches, or fast fashion watches will be considered, sorry Daniel Wellington.  

And finally, for breadth, I’ve chosen five price points and my reasons for choosing each particular watch. I’ve also decided to only mention brand new watches as the vintage watch market is mostly about perceived value (which can convolute things). So, without further ado, my “If I could only have one watch” winners.    

500 Dollars

At around 500 dollars I’d choose the Hamilton Khaki Field Mechanical. The watch, although not super expensive, has a lot going for it and truly punches above its weight class. It has a timeless design with beautiful neutral colors. It is Swiss made and from a legitimate watch company.  The watch can be worn at the beach on a nato strap or dressed up for a fancy dinner paired with a nice brown leather strap. Not only this, the watch features a mechanical movement, which means you get the satisfaction of winding it up every morning, this feature really adds to that nostalgic craftsman feeling. Finally, the dial is protected by sapphire glass, which means you can wear it while assembling the Ikea furniture for that girl you like and also take her out to a nice dinner all without the worry of it getting scratched!  


1000 Dollars

Things get interesting at this price point as there are a lot of cool watches you could choose. But at around the 1000-dollar price range, my choice would be the Sinn 356 Flieger Chronograph. Though not a Swiss made watch, this German made aviator’s chronograph is a thing of beauty. The dial design is elegant and symmetrical. and the Arabic numbers and bright lume give it awesome readability. The case is a lovely brushed steel and the dial design is timeless, making it just as awesome on a navy green nylon strap or with a black calfskin leather band. And last but not least, the Sinn 356 has a day function, a date function, and finally, a chronograph function; that’s three highly useful complications!    


5000 Dollars

The chronographs of all chronographs. The Omega Speedmaster Professional. The Moonwatch. If I could only have one watch and 5000 dollars to spend, I’d buy the Omega Speedmaster Professional and here’s why. For starters, Omega is an extremely well-regarded watch brand; this goes without saying and if you’re in doubt just ask George Clooney. Secondly, this watch has history written all over it; it has literally gone to the moon and back! Thirdly, this watch can be worn in any setting and everyone will still respect you for it. At the gym? The Hesalite crystal is light and bright. In the boardroom? Go ahead and time that meeting. At the local watering hole? Tell stories about where you’ve traveled and pull back the pints. Gents, at around the 5000 dollar range, you can not go wrong with the Omega Speedmaster.     


10,000 Dollars

Once you hit the 10,000-price range, a whole plethora of choices open up for you. If you wanted two watches for example, you could purchase a Rolex Datejust and an Omega Speedmaster. The Datejust on a jubilee bracelet for more formal occasions, and the Speedmaster on a beige nato strap for more casual settings. You could also get a Jaeger LeCoultre; the watchmaker’s watchmaker and a brand synonymous with horology and iconic timepieces, and also another watch. In theory, you could get an elegant LeCoultre Reverso Classique and also a rugged Rolex Explorer I, two awesome pieces for the price of around 10,000 dollars.

But, since we’re going with a single choice, the only choice at this price range must unequivocally be the Rolex Submariner. This watch is the world’s most popular watch for a reason and it has graced the wrists of many a distinguished gentleman. Former presidents, famous explorers, chief boardroom executives, courageous military soldiers, and even glorified bartenders, the Rolex Submariner is absolutely the most versatile and iconic watch ever. The funny thing is, even though it’s the world’s most popular watch, when you have it on your wrist, you just ooze class. There is absolutely nothing negative to say about this watch, the Rolex Submariner.


20,000 Dollars

If you are ever blessed with enough disposable income to afford a timepiece in this price range, you probably already know what you like and what you don’t like in a watch. But if I were to choose one watch, it’d be the Patek Philippe Nautilus. Imagined by the incomparable designer Gerald Genta, the Patek Phillippe Nautilus is an elegant and sturdy watch that looks equally stylish eating frog legs in a 3-starred Michelin restaurant as it does in a white tee eating a greasy burger. This versatility, coupled with Patek Philippe’s status as the greatest watch company in the world make this choice a no-brainer.



So there you have it!  My “if you could only get one watch” at five price points.  If you need more advice about watch purchases, which ones to buy, where to get them, and what to look for, email workman@the-workman.com for more guidance!  


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