Cheapest Rolex Watches for Men

By Patrick Fassler •  Updated: 07/22/22 •  8 min read

Like most luxury brands, Rolex watches vary significantly in price. From $6,000 to $60,000+, you can find a luxury watch from Rolex in just about any price range. With that said, most first-time buyers are looking more at the entry-level Rolex watches, including us, when we started looking for the cheapest Rolex watches for men. So let’s dive into the best value for your money on a new Rolex men’s watch. 

In this article, we will mainly focus on the cheapest Rolex watches for men that you can purchase brand new from the dealer. However, check out this article where we go over the most affordable used and vintage Rolex models if that’s more your style. 

Cheapest Rolex Watches for Men Brand New

Watches We’ll Cover

Rolex Oyster Perpetual 36mm

Retail Price: $5,800

Rolex Oyster Perpetual 36mm

The Rolex Oyster Perpetual is likely the best option you can find when looking for the cheapest Rolex watches for men. For quite some time now, the Oyster Perpetual has been the iconic starter watch from Rolex. While it may not have the long-term desirability of a more expensive Submariner or GMT Master II, the 36mm OP has seen a significant increase in demand over the last couple of years. 

In 2020, when Rolex released the pastel-colored dials, demand for the Oyster Perpetual went through the roof. While it may be one of the cheapest Rolexes at retail price, its demand has increased pre-owned prices by 100-150%. In most cases, they’re nearly impossible to find without at least an 8-12 month waitlist. For a first-time Rolex purchase, you could wait about a year to eighteen months for a new 36mm Oyster Perpetual. 

Rolex Oyster Perpetual 36mm Specs

If you’re looking to spend just a bit more (around $6,500), you can pick up a Rolex Oyster Perpetual Date 34. This would be another fantastic option to have in the Oyster Perpetual lineup. 

Even around the $10,000 price point, though, the Oyster Perpetual is still an okay deal. However, if you’re willing to spend more, I highly recommend looking into some of the lesser-known Rolex models on this list. It’s also worth noting that the color of the dial will change the price at the dealer. 

Rolex Air-King

Retail Price: $6,150

Rolex Air-King 40mm

The Air-King is another fantastic option for those looking for the cheapest Rolex watches for men. While the OP is a great starting point, the Air-King costs just a bit more. Because the Air-King is lesser-known than models like the Oyster Perpetual, they can usually be found a bit easier. 

Keep in mind, though, that Rolex doesn’t like clients hopping from store to store. For the most part, they like to see a customer purchase from the same dealer who is located closest to their residence. Trying to go straight to a dealer in another part of the state or nation may not work as effectively as some random forum threads may lead you to believe. If you’re serious about getting on the Rolex customer list, find one authorized dealer for your purchases. The relationship you build with them will help get you on the list for more Rolex models in the future. 

The Air-King is a great entry-level Rolex because of its more youthful design. Compared to the Date Just and Oyster Perpetual, the Air-King takes a more modern approach while respecting the heritage of aviation watches. While the OP is cheaper, I think the Air-King is a better watch overall because of its uniqueness in the Rolex lineup. 

The Rolex Air-King has a few good options under $7,000 retail, including the Blue Arabic dial and the Silver Stainless Steel at $6,150. 

If you’re looking for an Air-King Rolex, you can expect to wait around 9-14 months on average. While that may seem like a long wait, Rolex recently said they expect the John Mayer Daytona to have a waitlist of around 10 years, longer than it’s even expected to be in production. 

Rolex Air-King Specs

Rolex GMT-Master II (Batman)

Retail Price: $10,550 

Rolex GMT-Master II Batman

While it may seem like a big jump to go from watches under $7,000 to a GMT Master II at over $10,000, there is a method to the madness. For starters, it is still at the lower end of the Rolex price point. If you can find a new GMT Master II (Batman or Batgirl), you’ll be paying just over $10k. Their pre-owned value, though, is what really makes them affordable. 

GMT Master II Batman models are currently listing and selling in the $20,000 range on Chrono24 and eBay, meaning they’re currently a solid option for retaining value. While I wouldn’t necessarily say most watches should be an investment piece, I do believe there is a time and place for considering the residual value of a timepiece. 

When it comes to the GMT Master II from Rolex, it’s on the safer side. Being such a popular model, demand is extraordinarily high. It also has the iconic design that most people associate with Rolex. In most cases, I would say the extra $3k-$4k is worth it for this piece. I strongly believe this watch will retain most of its value for the next few years, as many people are still sitting on the waiting list for them. If you come across the chance to purchase one new, do it. 

I’m not suggesting you buy it and sell it right away. This can often get you blacklisted from buying new models from the AD (allegedly). However, I am suggesting that it’s more likely to hold onto its value than the others on the list, technically making it one of the cheapest Rolex watches for men. 

Even at this price, it’s cheap for a luxury watch of its quality and caliber. Typically, a first-time buyer can expect to wait 12 to 18 months for a GMT Master II new from the AD. 

Rolex GMT Master II Specs

Rolex Datejust 31

Retail: $6,850

Rolex Datejust 31 stainless steel - one of the cheapest rolex watches for men

The Rolex Datejust is another iconic entry-level Rolex. In fact, it’s probably the one most people think about when they look for the cheapest Rolex watches for men. I can’t fault anyone for that. For years, it has remained one of the simplest, most elegant watches in the Rolex lineup, and it’s a watch that will truly fit in nearly any formal and business scenario. 

A stainless steel Rolex Datejust is a fantastic watch for just about any collection, new or old. Because of its versatility, I would argue it’s one of the best one-watch collection pieces you can purchase. 

Datejusts are also very easy to find on sites like eBay and Chrono24 because of their popularity. For the most part, you should have any trouble finding one used if that’s the route you’re looking to take. Add to that, though, you can usually expect to wait roughly 6 to 8 months for a Datejust from the Rolex dealer – making it one of the shorter waits on this list. 

Remember, though, that the Datejust 31mm is a much smaller watch than the others on the list. If you have a larger wrist, it can easily swallow the small size of a 31m Datejust. However, it also makes the watch the easiest to wear on this list. 

Rolex Datejust 31 Specs

Buy the Cheapest Rolex Watches for Men New

That tops off our list of the 4 cheapest Rolex watches for men. Throughout the list, we’ve included some of the best values that Rolex currently offers for new watches; however, you can also find fantastic deals on the pre-owned market from sites like Chrono24, Bobs Watches, and eBay. In fact, most pre-owned watches on these sites have been authenticated by a professional, lowering your risk as the buyer. 

Overall, though, if you have the chance to purchase a new watch from a Rolex dealer, take it! Even with the waitlist, the value you get from purchasing a new watch from Rolex is unmatched by other brands at this price point, including OMEGA. If you think it isn’t worth the wait, I would still encourage you to put your name down on the list. It’s better to get the call one day than never to get the call. 

Patrick Fassler

🚗 Unhealthy Car Obsession ⏱ Semi-Healthy Watch Obsession 📌 Daytona Beach, FL

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