Up to 75% Off for Bulk Beads & Jewelry Making Supplies

Like “Tom Brady” and “misplaced pass,” “cheap” and “Rolex” aren’t typically associated with one another. Before it reaches your wrist, a Rolex passes through the hands of watchmakers, engineers, designers, and many other experts after being carefully created using only the finest materials.

Is it any wonder we struggle to discover the cheapest Rolex watches for men when it is said that each timepiece might take up to a whole year to make? I’ll respond in the negative: no, it isn’t. Though it can be difficult, finding something affordable is by no means impossible (especially if you know where to look).

We’ve been looking in all the appropriate places, as luck would have it. You won’t be forced to eat beans on toast for breakfast, lunch, and dinner once we gathered a collection of fairly great timepieces. For our list of the best Rolexes under $500 (albeit a somewhat generous list), keep reading.

Rolex Datejust 36 Automatic Watch at Jomashop


Rolex Datejust 36 Automatic Watch at Jomashop

Martin Luther King, Roger Federer, James Bond, and Winston Churchill. You must admit, it’s a rather remarkable (and somewhat random) selection of gentlemen. What do they all share, though? As you could have predicted, they have all worn Rolexes. Not just any Rolex, either. Their preferred watch is/was the Datejust, which is no surprise at all.

It’s undoubtedly one of the best luxury watches ever created, as well as one of the most recognizable. The Datejust is the ideal option for pretty much any occasion because it is ageless, recognizable, and all-around stunning. Our favorite of the group is this 36mm model, which features a stylish stainless steel case and the brand’s distinctive automatic movement.

Rolex Oyster Perpetual at WatchRapport

The Rolex Oyster Perpetual is discretely tucked away among a group of A-list celebrities (think the Daytona, Day-Date, and GMT-Master). Yes, it’s unquestionably impressive that rivals are vying for your focus and your hard-earned money. However, they Perpetually waits patiently for action from watch enthusiasts who are turned on in the shadows.

This late 1990s model is a wonderful entry-level alternative that costs just over $4,000 and is stylish and distinctive without being excessive or ostentatious. It provides practically all of the features you would expect from a high-end watch without being unduly expensive. With its elegant stainless steel case and white Roman numeral face, it will go with just about anything in your closet.


Rolex Air King Watch at Hodinkee

A Rolex requires a lot of planning and saving before purchase. For most guys, the starting price is frequently too expensive. How exactly do you go about making your ideal watch a reality on your wrist? Being the first to possess something is lovely, but it may also be the most expensive choice. You receive far more for your money when you shop in the used market.

This used Air King costs just under $7,000.00. So while it’s not quite cheap, it’s still one of the Rolexes that you can find. It’s from around 1999 and has a 34mm stainless steel Oyster case that fits smaller wrists well.

Rolex Datejust Wide-Boy Watch at WatchRapport

You’ll adore this used Datejust if subtle fashion is your thing. It exudes class with its stainless steel case and folded link Jubilee bracelet. The ideal amount of elegance is provided while remaining subtly subtle. It’s a great option for men who want a watch that can do it all (including quick pool dips, but not deep sea diving), without being overly dressy or sporty.

It fulfills all the necessary criteria in terms of adaptability, toughness, and style. And given the quality you receive, for a little under $8,000, it’s not a bad deal. It’s safe to say that you’ll wear it a lot because you can wear it to a wedding or out on the town.

Rolex Cellini Quartz Watch at Jomashop


Rolex Cellini Quartz Watch at Jomashop

The Cellini is the ideal shoe for those who appreciate leather and traditional fashion. This affordable Rolex for men is the kind of timepiece that doesn’t need to scream for your attention. It is simple and elegant. It currently commands all attention and likely always will. It will make a lasting impression on anyone wearing it (as well as anyone else who sees it on your wrist) because of its classic style and evident emblem of luxury.

It is just barely under the ‘cheap’ pricing range, coming in at around $6,000. It’s still one of the least costly Rolex watches you’ll find (and worth every penny) when compared to the other selections available. You will still need to start making some significant savings, though.

Rolex Oyster Perpetual Datejust 36 Watch at Jomashop


Rolex Oyster Perpetual Datejust 36 Watch at Jomashop

Owning a Rolex is frequently little more than a pipe dream unless you wait for a significant birthday or your income is comparable to that of Kendall Roy. You will undoubtedly need to sell your home in order to buy one if you add some diamonds and gold. Not nearly, however, you might have to cut back on your takeaway for a while.


You’ll have to fork over a little over $6000 to purchase this used 1987 Datejust. Since you’ll be wearing it the majority of the time, it does provide a reasonable entry point into the world of high-end watches. It has a jubilee bracelet made of 18kt yellow gold and stainless steel that exudes sophistication and superb taste.

Rolex Explorer II Polar Watch at Hodinkee

If you were to place the Rolex Explorer in a category, it would fall somewhere between a dress watch and a sports watch. Following the first ascent of Mount Everest by Sir Edmund Hillary and Tenzing Norgay, it was originally designed for explorers, hence the name. These days, it looks equally at home with your best formal shirts and sophisticated tailoring. In fact, wearing it only for your weekend walk can feel a little strange. However, each to their own…

It’s not exactly the most affordable Rolex for men, but at just under $12,000, it’s still less expensive than several other possibilities.

Image Credit: Google

Recommended2 recommendationsPublished in celebrity fashion, Jewelry