The Case For: A Classic Vintage Three-Watch Collection

We’re introducing a new series, addressing the watch community’s age-old challenge: the three-watch collection.

It’s an often-repeated question. Or maybe it isn’t, but it’s certainly a question worth some thought from us watch geeks: Can there be a three-watch collection? Can three watches be enough to satisfy any situation? The answer is yes, because really, one watch could be able to do it all. But you’re here because you probably have or want more than one watch, so let’s see if we can cap it at three.

This will be a series of collections loosely based on a theme, this one being “classic”. These are by no means hard-set rules — these are meant to be theoretical suggestions, or placeholder collection starters for beginners that might want a push. It’s fun to think through the philosophy of collecting, and even if you’re already stacked with watches (you know who you are), it’s worth thinking about how you would trim down your collection. These will also aim to be unisex collections that can fit anyone, regardless of gender.

What can your three-watch collection look like? 

We’ll go over some different versions as the series goes on, but let’s start with something classic. Say, one dress watch — for the office or the occasional formal occasion. One everyday watch, that’s your easy-wearing watch, something to put on without any thought. And maybe one sporty or “fun” watch, as a weekend watch or a cool, functional or beautiful conversation piece. All vintage. Not for any reason other than that’s just what we do here.

The criteria isn’t much more than that!

Start with an everyday-wearer

Since we’re dealing in classics, no classic collection is complete without a Rolex. We’re willing to bet we don’t really need to go into detail about why it’s an important house to bring to your collection. And while Rolex has a slew of iconic designs to its name, an absolute true classic with effortless everyday-wearing versatility is the Rolex Air King. Made all the way from 1957 to today, Air Kings come in a pile of reference numbers — but few are as lasting as the ref. 5500. 

This one in the shop has all the timeless elegance you associate with Rolex, in a classy and easy-wearing 34mm package. The wide blue slate dial makes it wear much larger than the diameter suggests, and the iconic Oyster bracelet is easily swapped for a leather strap for a less sporty look if you so desire.

Move into something more formal

This is a collection of vintage classics, and you’d be hard pressed to name a more iconic dress watch than the Cartier Tank. It’s graced the wrists of men and women far cooler than you or I will ever be — former First Lady Jackie O, Muhammad Ali, Princess Di, Andy Warhol and many others are the names you usually see attached to it. 

That’s Muhammad Ali with his Cartier Tank (Image via Getty)

This particular model take its style cues from Mr. Ali’s piece, and it’s hard to beat. It’s an ultra-wearable unisex size that’s easily “borrowed” by a partner without looking out of place, and it slips under a cuff or a sweater like nobody’s business. Watch people love using that phrase, but this thing really does disappear — and whether you’re at an event, at work, or at home (remember going outside?), your wrist will exude class.

End off with a bang

Now for something more fun, while keeping in mind the theme of this three-watch collection. You’d surely call the Omega Speedmaster a classic, but maybe not specifically think of this one when you think “Moonwatch”. While we could make the case (I almost did) that the Speedmaster is the perfect functional final piece of a classic collection, it’s worth looking for a more exciting spin on the 

This variation is called the Speedmaster MK40, and it’s a definitive product of the 90s — although unlike some other… eh, rough examples of 90s watches, the MK40 holds a shockingly strong design. When deconstructing the elements of this watch — the red chronograph hand, grey dial, blue and white subdial, yellow date pointer — it really shouldn’t work, yet somehow altogether it’s an aesthetic masterpiece. I don’t know how they did it. This piece has the added bonus of having become a popular reissued watch, making the original (this one) all the more sought after with that extra “fun” twist on a classic timepiece.

If you’re just starting out or are deep into this hobby, this is by no means a guideline you should be following, but rather a set of ideas to start you off in the right direction if the classic feel fits your personal style. Keeping these pieces in the vintage realm, all under the $4k mark makes them a jumping-off sweet spot for many, and all of these pieces (and similar references in their respective families) hold their own as a one, two, and three-watch collection.

Is there a category of three-watch collection you want to see us tackle? Send a message to @iamjoshcameron on Instagram or reach out through our Contact form. We’ve loved seeing your ideas so far and a huge thanks for sending this one in.