The Many Paths of a Rolex Collector

If Rolex could script the perfect collector’s journey, it would probably start simple. Your first step might be a steel Oyster Perpetual or an Explorer—something foundational, versatile, and reliable. From there, the natural “progression” might seem obvious: a Submariner or GMT-Master II, eventually a Daytona, and maybe a Day-Date in gold.

In reality, Rolex collecting rarely follows a straight line. For most people, the path is anything but predictable.

The First Rolex

Image Source: Huntington Company

Every collection has an origin story. Some start with an heirloom, passed down from a parent or grandparent. Others begin with a first purchase to mark a milestone—a graduation, a promotion, or just the desire to finally own a Rolex.

That first watch doesn’t have to be new. Many collectors are entering the brand through pre-owned and vintage models, especially with modern Rolex watches being tough to find at retail. Marketplaces like eBay, Bezel, and Chrono24 have become the starting point for countless first-time buyers. A four- or five-digit Datejust or a slightly worn Submariner might be the watch that sparks a lifelong obsession.

The Second Rolex and Beyond

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This is where things get interesting. Once you own one Rolex, you either stop—or you start thinking about the next.

Maybe your first Rolex was a current GMT-Master II 126712GRNR. A year later, you realize that while the dual-time function is useful, you want something quieter on the wrist. You trade it for a five-digit GMT-Master II or an Explorer II 16570.

Curved End Rubber Strap For Rolex Explorer II

A few years pass, and the itch returns. You convince yourself you need a dress watch under $5,000 and land on a vintage Datejust 1601. Then a Cellini Prince catches your eye. One becomes three, and suddenly you’re deep in a niche you never expected to explore.

Eventually, the collection reshapes itself. You sell a few, buy a Daytona 116500, maybe put it on a racing leather Everest strap, and—for a moment—you convince yourself the hunt is over.

A few years later, you convince yourself that you need a “dress watch” but don’t want to spend more than $5,000, leading you to a four-digit Datejust: a 1601. You like wearing an elegant watch but want something more unique, so you buy a Cellini Prince, opening the flood gates for you to buy every other configuration of the Cellini Prince out there (an interesting but respectable choice). Three months later, you sell all but one and buy a Daytona 116500. The same day, you buy a Racing Leather Strap from Everest, put it on your Daytona, and call it quits on collecting—you already have the perfect watch (I mean, look at that thing).

Why Rolex Captures Collectors

No matter how winding the path, choosing Rolex is about more than a logo on the dial. Every watch is built on the same promise that made the brand famous: durability and longevity. The Oyster case has been protecting movements for nearly a century, and that engineering makes Rolex a natural candidate for a lifetime of wear—and a future as a family heirloom.

Image Source: Analog:Shift

Over time, a Rolex collection becomes more than a lineup of references. It turns into a story: of milestones, detours, lucky finds, and a few regrettable flips. Every watch you buy and sell adds a chapter, and every scratch or stretch link marks the passage of time.

There’s no single roadmap to collecting Rolex. The journey is personal, shaped by the watches that resonate with you—and the ones you’re willing to chase.

If you’re looking to make your Rolex feel more personal along the way, our selection of integrated Everest straps is a great place to start. They’re designed to fit perfectly, whether you’re on your first Rolex or your fifteenth.