The Most Underrated Rolex Watches for First-Time Buyers (2024)

No watch brand even competes with Rolex for communicating success and prestige without saying a word. The Submariner, Datejust, Daytona and other models are immediately recognizable around the world, but the Rolex magic is in part based on exclusivity. They're expensive, and these are watches that many people aspire to own as a longterm goal.

A new, current Datejust starts at over $7k retail, and the Submariner is over $8k — and these are watches with only basic functionality, each in their most basic configurations. You're not going to get a Rolex for "cheap," but there are a couple ways to join the club for less dough than you might think. Depending on the model, vintage or pre-owned Rolex watches can be a good option — but there are also overlooked model families that not only offer strong value and the Rolex mojo but something a bit different from that oh-so familiar Rolex look.

The watches below each feature Rolex signatures (like the Mercedes handset and Oyster case) and similar specs, with three-hand automatic winding and no date. They're all under $7k and are much easier Rolex watches to buy than their more famous cousins.

Rolex Oyster Perpetual 36

The Most Underrated Rolex Watches for First-Time Buyers (1)

Rolex

The Oyster Perpetual is Rolex's entry-level mens watch, but it offers a true Rolex look and represents the brand's history in its purest form. Hearkening back to the first "waterproof" watch in 1926 with automatic winding added in 1931, this is the basis of most Rolex watches made since. It comes in different sizes, and for 2020 it got a new 41mm case and a ton of bright color options. The 36mm version, however, is perfectly wearable for many wrists and inline with modern trends, and it's slightly more affordable as well. Though the Oyster Perpetual has a formal look, it has the same 100m water resistance as the sportier models below.

Diameter: 36mm
Price: $5,600
Manufacturer Info: rolex.com

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Rolex Air King

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Rolex

Most people will probably think of the GMT Master II and Sky-Dweller as Rolex's aviation-themed watches before they recall the Air King. With its black dial and large Arabic numerals, the Air King stands out from the rest of the Rolex catalog with something of a military look and traces its roots to 1945 — though its modern design is younger and somewhat polarizing. The Air King currently doesn't use the latest generation of automatic movements (as the Oyster Perpetual above does), but it represents a lot of value as the entry point for the Rolex's sport watches. As a less popular model, the Air King perhaps says more about the person who chooses it than the more popular Rolex watches.

Diameter: 40mm
Price: $6,450
Manufacturer Info: rolex.com

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Rolex Explorer

The Most Underrated Rolex Watches for First-Time Buyers (3)

Rolex

For the same cost as the the Air King (unless you're springing for the new two-tone model), the Rolex Explorer offers a more universally palatable and uncontroversial option. Not to be confused with the Explorer II (which has a 24-hour-marked bezel and GMT hand), the plain-old Explorer is more basic but a handsome and well-balanced sport watch. With three-hand time-telling, it's recognizably Rolex and has the added benefit of its association with adventurers — most famously, Sir Edmund Hillary, who wore a "pre-Explorer" to the summit of Mt. Everest in 1953. It features a similar automatic movement as the Air King above and is a hair smaller at 39mm.

Diameter: 39mm
Price: $6,450
Manufacturer Info: rolex.com

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The Most Underrated Rolex Watches for First-Time Buyers (2024)

FAQs

Which Rolex is most desirable? ›

Sports watches have the best value increase

The most commonly sought-after Rolex watches include Rolex Daytona, GMT-Master(II), Submariner, and Sea-Dweller. The Yacht-Master is also a very popular sports watch, but not like the Submariner.

What entry-level Rolex holds value? ›

In conclusion, the Oyster Perpetual is the cheapest Rolex model, but it still holds its value and appreciation over time due to its reputation for quality, timeless design, and respect within the watch community.

What is the best Rolex watch for money? ›

Of all these top models, which Rolex holds its value the best? Many experts agree that the Submariner 16610 takes top marks in this category. And, despite the fact that gold prices often increase, the steel Submariner seems to be the most popular simply because of its timeless appearance and its durable reliability.

Which Rolex is easy to get? ›

Non-professional watches

This includes the Daytona, GMT-Master, Yacht-Master, Submariner, Deepsea, Sea-Dweller, Milgauss, and Air-King. With that said, all non-professional models are much easier to buy as the demand for them is lower, and the supply tends to be greater.

What is Rolex the cheapest model? ›

What's the cheapest Rolex? Prices can vary, but generally speaking the cheapest Rolex watch is the Rolex Oyster Perpetual, which has a starting price of around $5,000 if you're buying new, but can sometimes be found for cheaper if you don't mind buying a used model on the pre-owned market.

What is the waitlist for Rolex 2023? ›

So, the Rolex Daytona waitlist 2023 is likely to be at least 5 years if you're able to buy a Rolex Daytona. We've seen Covid pass through, World Cups end and start, markets rise and fall almost simultaneously and all within the time it takes to get your hands on a Rolex Daytona. It rests within good reason.

What is the most basic Rolex? ›

“Basic” Rolex timepieces often feature a time-only movement, such as the Rolex Explorer, Oyster Perpetual, Air-King, and variations of the co*cktail and Cellini. The Oyster Perpetual is probably one of the market's most popular and recognizable Rolex cheapest watches.

What is the most coveted watch? ›

In 2021, a rare Patek Philippe Nautilus with Tiffany Blue Dial Sold For A Record-Breaking $6.5 Million, showing the immense value placed on this model. According to renowned watch expert, Robert-Jan Broer, “The Patek Philippe Nautilus is a true icon and has become one of the most sought-after watches in the world.

Is any Rolex an investment? ›

The short answer is yes. Rolex watches have become a popular investment option for collectors and investors as they see their value increasing significantly over time. Here's why: First, Rolex is a highly respected brand with a long history of producing quality timepieces.

Does Rolex go down in value? ›

The short answer is yes, a Rolex is often worth that initial investment. Whether your watch will increase in value after purchase depends on the model you chose and the market, but most Rolex watches maintain a high resale value compared to other brands.

Which Rolex has the best value retention? ›

Which Rolex Watches Best Hold Their Value?
  • Rolex GMT-Master II. ...
  • Which Rolexes Have High Holding and Appreciating Value? ...
  • Rolex Submariner. ...
  • Rolex Cosmograph Daytona. ...
  • Rolex Day-Date. ...
  • Not All that Glitters is Gold. ...
  • Rolex GMT-Master II. ...
  • Profiting From A Rolex Watch.

Which Rolex does not lose value? ›

The Rolex Daytona has been worn by the greats, namely Steve Mcqueen and Paul Newman. Notably, Paul Newman's Rolex Daytona sold for a tidy $17.8m at auction. While you'd be hallucinating to think all Rolex Daytonas will sell for this, it is indicative that a Daytona still carries value.

Is there a watch better than Rolex? ›

Patek Philippe arguably owns the top-tier of high-horology. Once, the most expensive watch ever sold was a Patek Philippe with many complications and sold for over 11 million dollars, second only to a Rolex that was worn by Paul Newman.

What brand is comparable to Rolex? ›

Rolex's alternatives and competitors. See how Rolex compares to similar products. Rolex's top competitors include Breitling, Jaeger-LeCoultre, and Chopard. Breitling specializes in the development and manufacturing of watches.

Are Rolex prices starting to drop? ›

Prices for luxury Swiss watches are near the lowest in almost two years on the secondary market as Rolex, Patek Philippe and Audemars Piguet models continue falling from the record highs reached in early 2022.

Is it a good investment to buy a Rolex? ›

One of the major advantages of investing in Rolex watches is that they tend to appreciate over time. This means that they could bring significant returns on your initial investment should you choose to sell them down the line.

Does Rolex have affordable watches? ›

The most affordable Rolex range is the Oyster Perpetual family. This family dates all the way back to 1926 when Rolex paid its ground-breaking water-resistant case (the Oyster) with its automatic (perpetual) movement. The collection has been a mainstay in the Rolex catalog ever since.

How do you know if a Rolex is a good investment? ›

As with any luxury watch brand, some Rolexes hold their value better than others. Some of the best models to invest in include Daytona, Day-Date with the President bracelet, Milgauss and Submariner. These are some of the most popular watches in the world and they tend to hold and increase in value incredibly well.

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