Just like ‘Tom Brady’ and ‘misplaced pass,’ ‘cheap’ and ‘Rolex’ are two words that you don’t see together often. Thoughtfully designed and manufactured using the very best materials, a Rolex passes through the hands of watchmakers, engineers, designers, and many other specialists before it finds its way onto your wrist. 

It’s said that each individual timepiece can take around a whole year to make, so is it any wonder we struggle to find the cheapest Rolex watches for men? I’ll answer that for you: no, it’s not. However, while coming across something that doesn’t break the bank is a tough task, it’s by no means impossible (especially if you know where to look).

As luck would have it, we’ve been looking in all the right places. We pulled together a bunch of pretty awesome watches that aren’t going to leave you eating beans on toast for breakfast, lunch, and dinner. Keep reading for our round-up of the best Rolexes on a budget (albeit quite a generous one).

Winston Churchill, Martin Luther King, Roger Federer, James Bond. Quite an impressive (and admittedly random) list of gentlemen, wouldn’t you say? But what do they all have in common? You guessed it: they’ve all been wearers of the Rolex. But not just any old Rolex. The Datejust is/was their watch of choice (and we’re not surprised in the slightest).

It’s arguably one of the most recognizable luxury watches in the world (and the best ever made). The Datejust is timeless, iconic, and all-around beautiful—making it the perfect choice for pretty much any occasion. This 36mm model is our pick of the bunch, showcasing a sleek stainless steel case with the brand’s signature automatic movement. 

Plus, the luminous hands and index hour markers are a nifty feature that will be clear to see as you knock back the Bourbon at your favorite late-night bar.

Quietly nestled amongst a line-up of A-list headliners (think the Daytona, Day-Date, and GMT-Master) is the Rolex Oyster Perpetual. Yes, its undoubtedly impressive counterparts are yearning for your attention and hard-earned cash. But the Perpetual sits confidently in the shadows waiting for switched-on watch enthusiasts to make their move.

Classy and distinctive, without being garish or flashy, this late 1990s model is a fantastic entry-level option that will set you back a little over $4,000. It offers almost everything you need from a luxury watch without the overly excessive price tag. Thanks to its classy stainless steel case and white roman numeral face, it’ll look right at home with pretty much your entire wardrobe. Whether you’re dressing for a wedding, business meeting, or lunch with friends, this is your go-to timepiece.

Saving for and then buying a Rolex is no easy feat. The starting price alone is usually prohibitive for most guys. So how exactly do you go about turning your dream watch into on-the-wrist reality? While it’s nice to be the first one to own something, that can be the most pricey option. Shopping the pre-owned market certainly gets you a lot more bang for your buck.

This pre-owned Air King comes in right under $7,000. So it’s not spare change, but it’s definitely one of the most affordable Rolexes you’ll come across. It dates back to circa 1999 and comes with a 34mm stainless steel Oyster case that’s ideal for smaller wrists.

The luminous sunburst blue ‘explorer’ dial is sure to catch envious glances at your next family get-together, especially if it’s poking out from a navy tailored suit jacket.

If understated style is your thing, then you’ll love this pre-owned Datejust. Complete with a stainless steel case and folded link Jubilee bracelet, it oozes class. The perfect balance of offering a bunch of elegance without shoving it in your face. Not too dressy nor too sporty, it’s an excellent solution for guys in need of a watch that’ll do it all (including quick dips in the pool, but not deep sea diving).

From versatility to durability and style, it ticks all the right boxes. And for a hair under $8,000, it’s not a bad price considering the quality you’re getting. You can pop it on for a wedding or a night on the town, so it’s safe to say it’ll get plenty of wear.

For lovers of leather and classic style, the Cellini is where it’s at. Simple and classy, this cheapest Rolex for men is the kind of timepiece that doesn’t need to beg for your attention. It already has all the attention and probably always will. With its timeless design and iconic luxury obvious, it’s sure to leave a strong impression on any wearer (as well as anyone else who spots it on your wrist).

It just about fits into the ‘affordable’ category landing in the price category below $6,000. Comparing it to the other options out there, it’s still one of the least expensive Rolex watches you’ll find (and worth every cent). But that doesn’t mean you won’t have to start doing some serious saving. 

You could wear it with your finest formalwear, but it can also perfectly complement an everyday smart-casual look. If you’re looking for a versatile watch that will never fall out of favor, this is it.

Unless you wait for a big birthday or your paycheck resembles something similar to Kendall Roy’s, owning a Rolex is often nothing but a pipe dream. Add in some diamonds and a bit of gold, and surely you’re going to need to sell your house to afford one. Not quite—although you may have to go easy on the takeouts for a few months.

This pre-owned 1987 Datejust is going to cost you just over $6000. so it does represent a reasonable entry point into the world of high-end watches (especially when you’re going to be wearing it most of the time). Showcasing a whole lot of sophistication and good taste, it features an 18kt yellow gold and stainless steel jubilee bracelet. Plus, a classy champagne dial with yellow gold-tone hands and diamond hour markers. Bling on a budget.

If you were to categorize the Rolex Explorer, it sits somewhere between a sports and dress watch. It was originally made for explorers (hence the name) after Sir Edmund Hillary and Tenzing Norgay became the first men to summit Mount Everest. Nowadays, it looks equally at home with fancy tailoring and your finest formal shirts. In fact, it would probably feel kind of silly to only wear it while on your weekend hike. But each to their own…

Yours for a little under $12,000, it’s not quite the cheapest Rolex for men, but it is more affordable than some other options out there. The price tag is certainly more appealing once you take a look at the classic stainless steel with a Luminova dial and a durable Oyster bracelet. It feels sporty enough to wear with jeans and gym gear, but it will definitely impress at your next work conference. Telling time has never felt so good.

What To Look For When Looking For The Cheapest Rolex Watches For Men 

Model

From the Day-Date to the Submariner, there are many different types of Rolex models to choose from. Each starts at a different price point, with some being more affordable than others. For those searching for the cheapest Rolex for men, you should look at the Datejust, Oyster Perpetual, and Air-King. These styles aren’t going to hit your wallet as heavy (although, be warned, they’re still not exactly ‘cheap’).

Movement

Nowadays, Rolexes are either self or manually winding. However, this wasn’t always the case. The luxury watchmaker previously produced a small number of battery-powered watches called ‘Oysterquartz.’ This ended in 2001, but you can still find some of these models on the pre-owned market (and they tend to be some of the cheapest Rolex for men).

Material

Just as the metal of a wedding ring changes the price tag, your Rolex watch materials also play a big part in its value. The bracelet, dial, and bezel construction can all affect the price. Platinum is generally the most expensive, then gold and stainless steel. The cheapest Rolex for men are usually made from the latter. Bezels can be made from a variety of materials, including gold, titanium, and ceramic. But you may also find some dials can include extras such as diamonds.