In the world of fine watches, no brand comes close to the sheer power of Rolex. Year after year, this Swiss watchmaking giant continues to outsell all other high-end watch brands. Prized for its prestige, technical excellence, instantly recognizable designs, and value retention, there are so many reasons to choose Rolex when buying a luxury watch. The best way to find a less expensive Rolex is to shop the secondhand luxury watch market. At Gray & Sons, we carry a wide selection of pre-owned Rolex watches for men in great condition.

One of the benefits of buying used high-end timepieces, including Rolex, is, of course, the discounted price. In fact, you can save up to 70% off of retail prices when buying pre-owned watches. Plus, since Rolex watches are built to last over several generations, you are never sacrificing quality when you purchase previously owned Rolex timepieces. The only thing you lose is the heftier price tag.

Whether this is your first foray into luxury timepieces or you’re just looking for a more affordable Rolex to add to your collection. Here are our top picks for the best entry level Rolex watches for men.


Best Entry-Level Everyday Rolex Watch: Oyster Perpetual

Rolex Oyster Perpetual
Pre-owned Rolex Oyster Perpetual in stainless steel with a 18k white gold fluted bezel.

In 2015, Rolex unveiled their latest generation of the Rolex Oyster Perpetual and two years on, this particular model (ref. 114300) has been met with great success. One look at this relatively low priced Rolex and it’s easy to understand why. The Oyster Perpetual 39 has everything one needs from a men’s Rolex watch. A decent sized case at 39mm, a stainless steel body, a modern character, a clean legible dial, an automatic movement, and of course, that highly coveted Rolex name. Moreover, Rolex offers the Oyster Perpetual in a variety of colorful dials to suit anyone’s style. The straightforward three-handed Rolex is the perfect everyday luxury watch.

At retail, the Rolex Oyster Perpetual 39 is priced at around $5,700. In the secondary market, a used Rolex Oyster Perpetual can be found at much lower prices. If, however, you opt for older models, including vintage Rolex Oyster Perpetual references, you could save even more money.

If you’re looking for the one Rolex watch you can wear all the time without breaking the bank, then a pre-owned Rolex Oyster Perpetual is hard to beat.


Best Entry-Level Rolex Dress Watch: Datejust

Rolex Date in stainless steel.
Rolex Date in stainless steel.

If you lean towards a more classic aesthetic and want a dressier and more practical Rolex, then the Datejust fits the bill. The quintessential luxury dress watch, the Rolex Datejust has been the brand’s flagship model since its debut in 1945.

Variety is the name of the game with Datejust collection with an almost endless selection of sizes, materials, dial designs, bezel choices, bracelet options, and so on. Yet, the fundamental style of the Datejust is unmistakable thanks in part to the characteristic date window at 3 o’clock topped by the Cyclops lens affixed to the sapphire crystal.

Due to the vast options of the Rolex Datejust, prices vary greatly from just a couple thousand dollars to five digit figures. However, for the lowest priced Rolex Datejust models, go for stainless steel versions with as a little adornment as possible. In the pre-owned luxury watch market, you can find a traditionally sized 36mm stainless steel used Datejust for around $3,500. The larger 41mm secondhand men’s Datejust II steel model hovering under the $6,000 mark.

There’s a reason the Datejust has been so popular throughout its history. It just works in almost all situations and it’s a watch that proudly wears its Rolex badge.


Best Entry-Level Sporty Rolex Watch: Explorer


Rolex Explorer II in stainless steel
Pre-owned Rolex Explorer II in stainless steel

With its stainless steel construction, Oyster bracelet, black dial, Mercedes style hands, luminescent stick indexes, and oversized 3, 6, and 9 numerals. The Explorer is a sportier entry-level Rolex watch. Depending on the year, the Explorer ranges from 36mm for older models to 39mm for newer ones.

Rolex originally released the Explorer in 1953 in honor of Sir Edmund Hillary and Tenzing Norgay’s historic climb of Mount Everest. Although the Explorer boasts a rich heritage and a desirable design, it is still one of the more inexpensive Rolex models out there—particularly in the pre-owned Rolex market. Price wise, the latest Explorer, the ref. 214270, retails for around $6,500, while a used version will range from $5,000 to $5,500 depending on year and condition. However, discontinued secondhand Rolex Explorer watches are priced even less.

A Rolex watch that’s both historically important and sportier in style, the Explorer offers a solid value proposition.


When you’re ready to purchase a men’s Rolex watch, check out our inventory at Gray & Sons where we stock a wide variety of pre-owned Rolex models at affordable prices HERE.