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7 Cheapest Rolex Watches for Men, Least Expensive in 2024

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).

  1. Best Overall Rolex: Rolex Datejust 36 Automatic Watch

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.

  1. Best Entry-Level Rolex: Rolex Oyster Perpetual

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 $8,000. 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.

  1. Best Pre-Owned Rolex: Rolex Air King Watch

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.

  1. Best Stainless Steel Rolex: Rolex Datejust Wide-Boy Watch

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.

  1. Best Leather Rolex: Rolex Cellini Quartz Watch

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.

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