Your Next Rolex: How to Find the Perfect One for You

If you collect watches, Rolex or otherwise, you’ve likely asked yourself at some point, “what’s next?” Adding a new watch to your collection is a great way to mark a milestone, reward yourself for an achievement, or just indulge—all valid reasons (we don't judge). But before you make the leap, especially for a new Rolex, let’s break down the decision by lifestyle, budget, and personal taste to help you find the perfect fit.

Why Do You Want Another Rolex?

Everest Watch Roll in Crown Green

The first question to ask yourself is why you want another Rolex. Are you celebrating something special? Looking to fill a gap in your collection? Maybe you’ve always wanted a certain model and feel like it’s time to take the plunge. Your rationale matters; it can guide your decision making to make your purchase more meaningful.

Lifestyle and Design Preferences

Image Source: Hodinkee (Gishani Ratnayake or Chris Winters)

It’s important to consider which watches you actually wear and how you tend to wear them. Are you at a desk for most of the day? Are you a spelunker by trade? Are you looking for a "fancy dinner" watch? Whatever the case, I’d lean toward Rolex models with Oyster cases (most of them), as they’re incredibly durable, waterproof (or serviceable to be waterproof again), and span variety of aesthetics.

Budget Breakdown

Curved End Rubber Strap For Rolex Yacht-Master

Your budget will likely play a significant role in narrowing your options. Here are some jumping-off points for various budgets. With some exceptions *cough* Daytona *cough* you can find examples of these watches in higher or lower price brackets depending on condition, configuration, rarity, etc. Again, these are just jumping off points for you to find your next Rolex. 

Rolex Watches Under $10k

Image Sources: aBlogtoWatch, Wynn & Thayne, Perpetual Passion (left to right)

Oyster Perpetual: If you’re after something simple, the Oyster Perpetual (OP) is a great option, especially the new 41mm version. This is perhaps the most versatile watch on the planet: it’s clean, classic, and often colorful, available in many colors across multiple generations. With the exception of some particularly desirable colorways (e.g. the Tiffany Blue OP41), you should have no trouble finding a nice Oyster Perpetual under $10k. 

Vintage Datejust: Perhaps Rolex’s most recognizable silhouette, you can never go wrong with a four or five-digit Datejust. This could easily be your only watch: somehow just as appropriate at a beach as at a wedding. You get classic Rolex design elements like the fluted bezel and Jubilee bracelet, plus the convenience of a date complication. There are countless configurations to choose from and you can find solid examples in the $5-6k range. 

Modern or Neo-Vintage Explorer: The time-only Explorer is a versatile option with some interesting history (and/or marketing). If you like the 3-6-9 Arabic dial, it’s hard to go wrong with this watch. At 36mm (for most references), the Explorer is a versatile pick that won’t let you down, even at the top of Mt. Everest.

Rolex Watches $10k-$20k

Image Sources: Instagram @rolexdiver, The Marin Vault, Reddit u/AlsoKnownAsJohn (Curved End Rubber Strap For Rolex Sea-Dweller 4000)

Submariner: While you can certainly find a Submariner under $10,000, above that threshold is where you’ll find the good stuff. I’m partial to five-digit Subs like the 14060(M), but your choice will ultimately come down to personal preference. Check out our recent article to learn more about what’s “the best” Rolex Submariner.

GMT-Master: From the classic “Pepsi” (in its many forms) to the new and understated black-and-grey “Bruce Wayne,” the GMT-Master line offers practicality with its dual hour hands and charm in spades. Personally, I love the ‘Coke’ GMT-Master: see our buying guide here.

Sea-Dweller: For those who love the Submariner but want a bit more wrist presence, the Sea-Dweller is the way to go. The deeper-diving sibling comes in many forms, but for my money, the SD4000 (ref. 16660) offers great value at its pre-owned price.

Rolex Watches $20k+

Image Sources: Oliver & Clark, Wynn & Thayne

Daytona: The Rolex Daytona remains one of the most sought-after chronographs–and really just watches–in the world. As you cross the $20,000 price point, you'll have your pick of the litter with Zenith Daytonas, Ceramic Daytonas, and as you continue to climb the ladder, vintage Daytonas.

Day-Date: The President’s Watch is a grail for many. It's hard to not love that curved 12 o'clock day aperture. Again, while you can get a Day-Date under $20k, you’ll find nicely-maintained vintage and modern Day-Dates above that threshold. The pictured example is a ref. 118238. To me, a yellow gold or platinum Day-Date is the endgame Rolex.

Vintage vs. Modern

Image Source: Hodinkee

One of the beauties of Rolex is that its watches are built to last. Thanks to the Oyster case’s durability, even decades-old models can remain waterproof and robust when properly maintained. The movements inside–going back decades–are fully serviceable and will continue to run accurately, again, when properly maintained.

Vintage Rolex models often represent excellent value and carry a unique charm, but they require some homework to get a good one. Ensure the condition is sound, and find a trusted dealer to avoid surprises. If warranties or factory-new finishes matter to you, a modern or pre-owned piece from an authorized retailer might be the better route.

Keep The Focus On You

Image Source: Analog:Shift

While trends can be tempting, they shouldn’t dictate your decision. A Rolex should be a long-term investment in enjoyment, not just a financial asset. Focus on what you love: the aesthetics, the story behind the model, and how it fits into your lifestyle. Resale value is secondary—buy a watch that you’ll want to wear, not one you’re afraid to scratch.

Final Thoughts

Choosing your next Rolex isn’t just about adding another piece to your collection—it’s about finding a watch that complements you and your lifestyle. Regardless of your budget or rationale, your next Rolex should be the one you want to wear most.

Already have your dream Rolex? Consider pairing it with an Everest strap for a whole new wearing experience. Available for most Rolex models, Everest Curved-End straps– available in rubber and leather–breathe new life into your watch while protecting its original bracelet.