Want to Buy a Luxury Watch? Read These 7 Pro Tips First

PERHAPS YOU’VE hit a milestone—a new job, an anniversary, a first pregnancy. Perhaps you’ve stumbled upon a watch enthusiast’s Instagram feed and are intrigued. Perhaps you’ve simply looked down at your naked wrist and thought, ”Something’s missing.” Whatever the reason, you’ve resolved to buy a watch. A nice one. Not an Apple Watch or a Swatch—not that there’s anything wrong with them—but something that requires a sizable budget and a commitment. But where to begin?

To make a bad watch joke, it’s more complicated than you might think.

“There are so many facets to buying a watch,” said Paul Boutros, head of Americas for watches at Phillips auction house. “Whether you choose vintage or modern, it could seem like you have to figure out how to climb Mount Everest when you’re starting.”

Mr. Boutros recommends first deciding on a brand, then a model—both choices that require serious research. Reliability is paramount, but understanding what each timepiece telegraphs is also key. If you project an implausible mix of outdoorsiness and sophistication—or wish you did—a luxe dive or sports watch might be for you. If you’re a glamorous type who’s back on the gala circuit, a watch dripping in diamonds could prove most “functional.” If your personal brand is timeless chic, the Cartier Tank collection is up your alley. Omega’s Speedmaster, meanwhile, “kind of marks you as someone who likes watches,” said Adam Craniotes, co-founder of RedBar, a watch-enthusiast platform, even if it doesn’t carry the hype of a Rolex Daytona or Submariner. The Speedmaster was the watch worn on man’s first trip to the moon, immortalized in Ron Howard’s 1995 film “Apollo 13,” and is now favored by President Biden. Ultimately, your watch will be a matter of individual preference, and the website Hodinkee, a popular watch-lover’s platform, is a good place to glean essential information during your search.

But even if you select a timepiece from the tippy-top tier of heritage Swiss watch houses—like Rolex, Audemars Piguet, Patek Philippe, Omega, Vacheron Constantin—you can’t always proceed without understanding the workings of the insular horologic world. For example, one cannot simply waltz into any authorized dealer (AD) and walk out with the most popular models, which include the Rolex Submariner and Daytona, the Patek Philippe Nautilus and the Audemars Piguet Royal Oak. A combination of hype economy and Swiss supply machinations has made these stainless-steel sports watches the ultimate luxury flex, nearly impossible to get firsthand. Wait lists are epic and are reserved for those who have relationships with the house or the AD. “If you don’t have a history of purchasing with them, you’re just putting your name down. They’re not putting you on the list,” said Mr. Craniotes. The demand for these enviable timepieces has spiked on the secondary (resale) market.