These are the best, cheapest Rolex watches (read: affordable) money can buy. Of course, just because something is cheap doesn’t necessarily mean that it’s worthwhile. When I talk about affordable, I mean they’re worth putting your money into because these are watches that are timeless, that are extremely versatile, very robust, and ultimately I think they can get the job done in any collection.
So what we have today is a selection of watches that I feel are some of the absolute best Rolex watches money can buy.
#1 Rolex Explorer 1 Reference 14270
The Rolex Explorer 1 reference 14270 has a slightly more classic case size of 36 millimeters but a perfect aesthetic. It’s a time-only watch that’s super legible given the Explorer 3, 6, 9 dial. It’s a watch that could do absolutely anything as it’s extremely robust at 100 meters of water resistance.
The watch itself features a very clean and very legible black dial. Again in 36 millimeters, I think it’s really a perfect size as a kind of casual or even semi-formal kind of Rolex watch. On a metal bracelet, makes it extremely practical. One thing to note about these older reference Rolexes is the versatility that they provide. You can change out this bracelet, put it on a leather strap, or even put it on potentially a perforated rubber strap and completely change the look of the watch. This simple, robust and versatile watch is first up on our list of the best, cheapest mens Rolex around.
This gives you an unlimited combination of choices, especially since this aesthetic is so clean and classy that it really will go with just about any strap you choose to put on it. Overall, these watches can be had pre-owned for about the $7,000 price point, or any Rolex under the $10,000 price point is certainly a great value, but especially for something like this that is extremely versatile. Because it’s a time-only watch you can just wind set and wear, this is really perfect as a do anything, go anywhere kind of watch.
#2 Cheapest Rolex GMT-Master (16710 & 16753)
Next up is my absolute favorite model line from Rolex, and that is the GMT-Master line. I feel that Rolex has really perfected the GMT complication and has created a design that is not only timeless but extremely functional and distinct and really the best GMT on the market. I really can’t think of a better travel watch for the price. I want to present to you two GMT variants that I think are absolutely great and very undervalued in the current market. They are, these pre-ceramic GMTs, Reference 16710, and of course Reference 16753.
Back to basics: What is a GMT Watch?
The reference 16710 here sports a Pepsi-style bezel. You can get it also in an all-black bezel, or in a coke bezel, all of which I think are absolutely amazing watches. The great thing is the functionality of it having of course a GMT complication, but also the versatility. At the end of the day, you can pop out the bezel, swap it out with, for example, a black bezel if you have a Pepsi or a Coke bezel, and the same with the other three, and also swap out the bracelet.
These are what are known as holes case Rolexes, which means there are actually holes on the side of the case, which allows it to be extremely easy to pop off the bracelet and pop on potentially a leather strap.
This is a watch that you can really have an infinite number of style combinations with, which is something that simply modern Rolexes and modern GMT-Masters just can’t provide. This versatility, along with the price, makes the 16710 an excellent choice if you’re seeking an instantly recognizable classic among the cheapest Rolex watches you can find. Another thing that I absolutely love about these vintage or neo-vintage GMTs is they’re extremely slim profile, which actually wears a lot slimmer than the modern GMTs.
I also love the 16753 Rolex GMT-Master II, better known as the Root Beer. This kind of two-toned bezel with kind of brown and gold, along with that almost auburn-like dial is just an absolutely stunning combination. These are ones that are super underrated, especially considering where the modern Root Beers trade at. I feel that there is a charm to these that is really lost on the modern GMT-Master II references, in particular the Root Beer.
In terms of price, 16710 in steel, again, depending on the year, depending of course on the contents, you can get approximately in the $12,000 to $15,000 range. Whereas a Root Beer like this, again, probably around the same thing, about the $12,000 to $15,000 range depending on the year, contents, and condition. When you think about it, these are just amazing watches overall. You get a super functional complication in an aesthetic that is very versatile and that you can change up on the fly and easily, ultimately you get a watch that is a timeless classic. These are never going to go out of style.
#3 Rolex Milgauss 116400GV
The next watch is from one that I feel is the most quirky and distinct model line from Rolex, and that is the Rolex Milgauss. The modern Milgauss references have a number of stylistic characteristics that distinguish them, such as of course, the very quirky and distinct lightning rod hand, not to mention the GV glass. Now, one thing to note is that Rolex patents almost everything that they do, but they never patented the GV glass for the actual Milgauss line, which is very surprising. I think it’s just a testament to how difficult it must be to actually create that GV glass that they figured that if somebody else can do it, then go right ahead.
See it on the Wrist: Rolex Milgauss Watch 116400GV Wrist Roll
Overall, I really like the Milgauss model line because of its truly unique characteristics and design, but also because it is a super functional watch, namely that it’s time-only and it’s built for purpose. It was that original tool watch that was meant as something that was amagnetic. Now, while that complication is technically obsolete because modern Rolex watches are fitted with silicon parts, that history is still ingrained in the Rolex Milgauss model line.
The Rolex 116400GV in particular with that stunning Z-blue dial, as it’s known, is so beautiful. I think with age, this will turn into a beautiful, almost turquoise-style dial that will just age beautifully. I think it will truly be one of those future collectible Rolexes over time that people will only appreciate once it’s no longer produced.
Price-wise, these will vary depending on if you’re getting the black GV or the blue GV. In the blue, you’re looking around the $11,000 to $13,000 range depending on the year, contents, and condition. I have to say I think that is a phenomenal value overall considering the distinct design that you’re getting and also the rich history of the model line itself, and considering the fact that you’re getting what I feel is a unique watch from Rolex. It’s unlike anything else in their catalog, and in my opinion, it’s really unlike anything else on the market today.
#4 Cheapest Rolex Day-Date (references 18238 and 18239)
Last but certainly not least is a model line that Roman has been singing its praises for many years, and I couldn’t agree more with him. It is those neo-vintage and vintage Day-Dates, the Reference 18238s and 18239s. These present themselves as phenomenal value proposition overall. You’re getting an all-gold Rolex in a gold case, a gold bracelet with day-date complication, and in a model line that is arguably one of Rolex’s most iconic for about a $17,000 to $20,000 price range.
Read more: The Ultimate Rolex Day Date Price Guide
When you think about that, that is roughly where modern GMT-Master IIs are trading at, namely in the Batman and Pepsi configurations. At that price, to be honest, I’d almost want an all-gold watch instead.
Not only is it extremely functional, but it’s also super distinct given the presidential bracelet that this watch is on. I love all the different dial variations that you can get, obviously, all of which will impact the price, but you can get things such as stick dials, Roman dials, diamond dials, you can get even myriad dials. There are so many different combinations that you can get in the Rolex Day-Date, particularly in the 18238 and 18239 references.
These references won’t look like the cheapest Rolex around, but you won’t do better on value for an all gold Rolex. What makes it awesome is that you can alter it according to your budget and according to your sense of style. You can grab one at the $17,000 price point to $20,000 for more muted designs, and $20,000 to $25,000 depending on the dial that it comes with and whether it has a factory diamond setting, I think you really can’t go wrong. Especially when you consider where modern Rolex watches are ultimately trading at today, these being, in my opinion, a lot rarer and a lot more valuable just because they’re an all-gold watch on a gold bracelet.
Another thing to note about these vintage day-dates is their size. These are 36 millimeters, which is technically a more classic size, but if somebody like Tony Soprano or James Gandolfini could rock a Rolex Day-Date, frankly, I’m sure that everybody else can pretty much pull it off. Not to mention the fact that size trends for watches are actually declining. People are gravitating more towards the 40 mil case sizes and below, again, whereas previously they used to be 42mm plus.
Personally, I’m all for the smaller case size trend. I do feel that 38 to 40 millimeters generally is that sweet spot, but I wouldn’t neglect these 36 millimeter case size watches because ultimately these wear a little bit bigger than their size actually describes them to be. At the end of the day, these are timeless icons that will continue to endure for many years and will truly outlive us.
Takeaways on the Cheapest Rolex You Can Buy
These are what I believe to be the best approachable Rolex watches for really any collection, be it for somebody who’s just getting into the hobby or somebody who has a strong watch collection of 10 plus watches. I think these are all versatile, all have their unique characteristics and all represent a great value in the modern watch market. At the end of the day, I think that these older model Rolexes, and even for example, these current production Milgausses all represent a great value overall that are truly unique and truly add a lot of character to any watch collection.
Let me know down in the comments what you feel are some of the most approachable and best affordable type Rolex watches to add to any collection. Of course, guys, please let me know down in the comments what videos you’d like to see in the future. My name is Marco, and guys, I’ll see you in the next one.
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