A Happy Watch Collection is One with Two of Everything

The most elemental question—and the most important one after “Should I sell my house to buy that watch?”—is:

What watches should I collect?

Should I specialize in just one brand, such as Patek Philippe, Rolex, or Seiko? Should my watch collection primarily showcase watches from a particular country, say Japan, China, or England? Should I focus on watches with more than three complications or ones that were made prior to the Quartz Revolution? Should I buy only watches that I can't really afford, or should I pursue a varied cost collection?

Or should I randomly collect whatever watches I like?

Actually, those are all fine approaches to watch collecting. There are so many different kinds of watches—different designs, prices, manufacturers, technologies, shapes, sizes, movements—that any criteria you choose, even if none at all, is fun.

But I have another suggestion: Collect a vintage version of every watch you have or will have. I call this historical-pair watch collecting.

One of the beautiful things about watches is that most brands have a long, colorful history. Most watch companies have been here in one form or another for decades: Owning watches made by the same company half a century or so apart envelopes you in that company's history. You can intimately know the company's evolution of design, how the movements have changed—and what's stayed the same, too. Owning two of every watch makes you more of a watch expert.

And it's enjoyable. Some days you might feel in a modern mood, so you put on your 2015 Breitling Transocean. Other days, you might wake up with nostalgia in your eyes, so your 1950s Breitling Premier finds its way to your wrist.

Today might be the day that your Omega Speedmaster White Side of the Moon arrives, but tomorrow you can put on your Omega Seamaster Deville, the kind that Don Draper wore in Mad Men, enabling your mind to wander back through time to the 1960s.

The modern watch you buy today will become a vintage watch in a few decades, so you can buy another and continue your journey through watch history.

Here are two examples of historical-pair watch collecting.

One of these:

And one of these:

Photo from Rolex

One of these:

Photo from Wikipedia

And one of these:

Photo from Hamilton

Now, if only it were fashionable to wear two watches at a time—one on each wrist—collecting watches would become even more fun.