Buying Your First Rolex

When you’re ready to buy your first Rolex, combing through all your options can be daunting. Classic or sporty? Steel, two-tone, or gold? Mid-size or large? Modern or vintage? The choices are almost endless. To simplify the decision of which is the best Rolex to buy, here are three models to consider.

Rolex Air-King

The Rolex Air-King is one of the company’s oldest models still part of the brand’s catalog today. Originally launched in 1945 as a tribute to Royal Air Force pilots during World War II, the Air-King is the only model that remains in production from Rolex’s “Air” series of timepieces—which included the Air-Lion, Air-Giant, and Air-Tiger. The Air-King itself was discontinued for a few years; Rolex revived the line in 2016, completely revamped and quite different from its predecessors.

Rolex Air-King

The Rolex Air-King has had the reputation for being a solid entry-level luxury watch and makes a great choice for a first Rolex. Older versions of the Air-King sport clean and straightforward dials housed in a 36mm stainless steel Oyster case. Whether you opt for an earlier model or the newest version, the Air-King’s interesting history coupled with its timeless appeal and attractive price-point makes it a top contender as the best first Rolex to buy.

Rolex Oyster Perpetual

The Rolex Oyster Perpetual is a time-only watch that celebrates elegant simplicity and alluring symmetry. From its COSC-certified automatic mechanical movement to its classic Rolex shape, the Oyster Perpetual ticks all the right boxes as a first Rolex nominee.

Rolex Air-King

Not only does the Oyster Perpetual collection come in a variety of different sizes, dial designs, bracelet choices, and metal possibilities—it’s a watch that never needs to be taken off. Appropriate for day and night, casual or formal, the Oyster Perpetual’s understated style is ideal for daily wear. If approachability and versatility is key, then the Rolex Oyster Perpetual is hard to beat as the best first Rolex.

Rolex Datejust

The most “Rolex” of all Rolexes, the Datejust is the brand’s flagship model. Iconic and instantly recognizable thanks to its characteristic date window at 3 o’clock magnified by the famous Cyclops lens, the Datejust symbolizes the company’s quest for innovation. When it made its debut in 1945, the Datejust was the first automatic wristwatch to show the date on the dial. And its largely-unchanged design illustrates the Datejust’s enduring allure.

Rolex Datejust (two-tone)

The Datejust is by far Rolex’s most varied collection for men and women, ranging from discreet stainless steel models with clean dials to full gold versions with diamonds. A step up from basic entry-level Rolex watches, the Datejust is the best first Rolex for those looking for a watch with practicality, heritage, and lasting luxury.


Prized for their classic designs and varied style options, the Air-King, Oyster Perpetual, and Datejust are some of the best first Rolex watches to invest in. Plus, with their friendly price points, these particular models are an accessible ticket into the Rolex watch club.

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Crown & Caliber is the smartest way to buy or sell a luxury watch. As an exclusively online marketplace for pre-owned timepieces, Crown & Caliber exists to ensure that when it comes down to the final transaction, buyers and sellers can both win. For sellers, we do all the legwork of valuating, marketing, and selling—for buyers, we put trust back into the act of purchasing sight-unseen with our servicing and authentication process. By emphasizing transparency and placing value on quality, Crown & Caliber has become the preferred marketplace for watch collectors and casual enthusiasts alike.

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