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.”

“ ‘There are many facets to buying a watch. It seems like you have to figure out how to climb 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.

THE BIG TIME Five classic watches worth a splurge. From left: Reverso Tribute Nonantième, $40,500, jaeger-lecoultre.com; Datejust 36, $8,550, rolex.com; Tank Louis, $10,700, cartier.com; Calatrava, $40,810, patek.com; Royal Oak ‘Jumbo’ Extra-Thin, $105,400, audemarspiguet.com.

THE BIG TIME Five classic watches worth a splurge. From left: Reverso Tribute Nonantième, $40,500, jaeger-lecoultre.com; Datejust 36, $8,550, rolex.com; Tank Louis, $10,700, cartier.com; Calatrava, $40,810, patek.com; Royal Oak ‘Jumbo’ Extra-Thin, $105,400, audemarspiguet.com.

Photo: Suzanne Saroff for The Wall Street Journal; Sittings Editor: Jessica Gibbs

The list price of the Nautilus 5711, a basic (but in-demand) three-hand watch with a date function and stainless steel case—no precious metals—is about $30,000, “a lot of money, let’s be honest,” said Mr. Craniotes. “If you want to buy one tomorrow, you can expect to pay close to $100,000, and that’s on the secondary market…you can’t get one through a dealer.”

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The secondary market consists of outlets like eBay and Crown & Caliber, an online platform where individuals and dealers can buy and sell luxury watches. Then there’s the gray market—for example, the Diamond District on 47th Street in Manhattan, which, in some respects operates like an old-world bazaar full of unspoken rules (think “Uncut Gems”). Of course, it’s possible to find a stellar timepiece there, but it’s also tricky territory for novices to navigate, so watch insiders recommend that only watch insiders go gray.

When it comes to watch-world tips, that’s just the beginning. For instance, it’s important to be versed in leading auction houses like Phillips; hot new watch brands, such as Ming, which launched in 2017 out of Kuala Lumpur; and hot independent brands, like F.P. Journe, named for founder François-Paul Journe, who has earned a reputation as a mercurial maestro.

Sure, there’s a lot to learn—but we’ve assembled a cheat sheet. Here, seven tips to help you find your next top-notch ticker.

Illustration: Errata Carmona

Be Realistic About Your Forever Watch

“If you have any doubt, definitely don’t buy it,” said Cara Barrett, a former editor at Hodinkee and the founder of Parchie, a company that makes children’s watches that she plans to launch this summer. “It’s kind of like a pair of shoes that are a little too small. You’re never going to wear them.”

To confidently decide what watch will suit you best, Ms. Barrett suggests asking yourself a few questions, like “What’s your budget?”, “Do you want to wear it every day?” and “Are you active?” These queries seem simple, but thoughtful answers will help narrow your search. And being able to clearly relay your needs to salespeople will help them guide you, too.

Ms. Barrett also advises considering your professional environment before you buy—i.e., do you work in an office and, if yes, what’s the culture like? “That will [dictate] how flashy [or] how not flashy you want to be,” she said.

Other helpful rules of thumb: Go with a timepiece from a Swiss heritage house and buy from a trusted dealer (if not from the house directly) to ensure you have recourse and service options. And always try it on first.

Make Friends at Your Chosen AD

Despite having a name that brings to mind duty-free shopping, Watches of Switzerland is one of the best ADs going, along with Wempe. These international stores’ salespeople are extremely knowledgeable, can guide you toward alternatives to big houses’ most sought-after models, and educate on fancy complications such as perpetual calendars. The watch business is a relationship business steeped in tradition and in-person exchanges with champagne and such. Become friendly with your salespeople at a big AD—that could be as simple as staying in touch after buying your starter watch or popping in now and again to see new models. They can help you navigate wait lists (especially the aforementioned epic ones) and other watch-world esoterica.

Don’t Be Intimidated by Watch Auctions

Any notion of auctions’ being an elitist event for the super rich is “a misconception,” said Mr. Boutros. He noted that most Phillips auctions are open to the public and do not require tickets for in-person attendance. And at some auctions, he said, opening bids can start as low as $500. Phillips sources worthy watches at nearly all price points. “We often are seeking the best of the best from those lower-priced models that we personally would buy ourselves,” said Mr. Boutros. The first step to buying a watch at auction is simply knowing when the auctions are—information that’s readily available online. There are two seasons for Phillips’s live auctions, spring and fall, with live events held in Geneva and Hong Kong in May, June and November and a once-a-year special sale in New York in early December. The watches go on tour in the lead-up so potential clients can see them, handle them, get a sense of their condition and ask questions. All watches are supremely vetted, so clients can rest easy.

How an economic principle called the ‘snob effect’ allows watchmakers to charge sky-high prices The Wall Street Journal Interactive Edition

If You Bargain Hunt, You’ll Probably Get Screwed

Don’t look for a deal. Don’t hit the gray market. If you’re buying on eBay or from a secondary dealer, Google the model and reference number and see what established resellers are charging. Fake watches aren’t common, but models that have been damaged, serviced or repaired with new parts (which can depreciate the value) are. Research the seller and verify that the watch is in that person’s possession. Mr. Craniotes suggests asking for a picture of the watch with today’s newspaper (extreme, but also effective). “Any legitimate seller will expect this and will not take offense that you are having them jump through a few extra hoops,” he said. “The second you get a funny feeling or the person’s not responding in the way you want, walk away. There’s another watch for you.”

Switch Things Up With Your Second Watch

Congratulations. You have your everyday staple and it’s time to branch out. The goal, said Ms. Barrett, is to create “different categories within your collection” while sticking to your aesthetic. Maybe that means investing in a dress watch, such as a Bulgari Serpenti or a Patek Philippe Twenty~4 with diamonds. Or maybe it’s a gold watch with an alligator strap that can be swapped out for one in patent leather or calfskin to change the mood. Don’t be afraid to have some fun with your round-two pick.

Illustration: Errata Carmona

To Impress Watch People, Become a Watch Person. Or, Buy a Hot Watch.

If you want to woo the watch set, get on their level. Fall down the rabbit hole, Alice. Take pleasure in researching the matrix of complications—mind-boggling composites of tiny gears that are the essence of timekeeping. Study up on watch-world celebrities like Aurel Bacs, who founded Phillips in Association with Bacs & Russo with his wife, Livia Russo. It will take a while to get indoctrinated.

Alternatively, you can take a shortcut. Mr. Craniotes recommends buying a watch from F.P. Journe, “the current darling of the indies,” whose prices start at around $16,000. Or you can search the resale market for limited editions—especially those with intricate backstories you can tell during small talk. In this respect, the 2015 Omega Speedmaster Silver Snoopy Apollo 13 45th Anniversary Edition is especially desirable. It honors the Apollo 13 mission’s 45th anniversary and depicts Snoopy and a thought bubble declaring: “Failure is not an option,” a line attributed to Gene Kranz, Apollo 13’s flight director.

Funny thing is, he never said that. Ed Harris did when he played Kranz in the 1995 movie. But Kranz loved it so much that he titled his memoir “Failure Is Not an Option.” Snoopy’s watch-face cameo is a reference to the Silver Snoopy, an award NASA gives for outstanding performance contributing to flight safety and mission success. NASA astronauts on the Apollo 13 mission all received an Omega Speedmaster Professional Chronograph, and it helped save the crew after an oxygen tank ruptured and jeopardized their mission. The 2015 list price was $7,350. Today, it’ll cost you about $50k—if you can find one. Only 1,970 were made, a nod to the year of the mission (and another fun tidbit for chitchat).

It Never Hurts to Think About Resale

Even if you plan on passing your watch down to your grandkids, keep your options open. With that in mind, hang on to the original authentication papers and box. Those will add significant value when reselling. Particularly sought-after watches from such houses as Patek Philippe, Audemars Piguet and Rolex can have resale values that far exceed their list prices. You can sell a luxury watch on eBay or to Crown & Caliber or with popular online consignment stores like TheRealReal. That site will suggest a list price, which you can accept or decline. If using eBay, do some googling to find the average cost at resale. You can also trade in your watch at an AD, get something new and pay the difference—kind of like a car, and for around the same price.

The Wall Street Journal is not compensated by retailers listed in its articles as outlets for products. Listed retailers frequently are not the sole retail outlets.