For many watch collectors, a common defining point in their journeys is the moment when each must choose his first Rolex. As the luxury watch marque of reference for connoisseurs and a transcendent brand name that achieves mainstream recognition, Rolex appeals equally to new and experienced watch collectors. Those choosing their first Rolex tend to fall into two groups: first-time luxury watch buyers and seasoned collectors who seek to add a Rolex.


First-time watch buyers gravitate toward Rolex watches because in many cases, the name “Rolex” is the first these individuals ever associated with luxury timepieces. Familiarity gained via advertising, word of mouth, and Rolex’s ubiquitous dealer network entices many of the watch-curious to seek a crown-bedecked reference as soon as circumstances permit. For these watch buyers, Rolex may be a default brand selection, but it’s also a smart one. The challenge is learning enough about the Rolex line to choose the right model.

Lasting satisfaction is important to first-time luxury watch customers, and “first watch” acquisitions often arrive early in life when one’s budget will not support do-overs for mistakes made. The best way to determine the best Rolex for an individual is to go low-tech and visit a physical showroom. Peace-of-mind comes from ensuring that a watch fits and feels right on one’s actual wrist. The ergonomic element often is overlooked when comparing the more commonly discussed appearances, features, and prices of Rolex watch options. If shopping online for a preowned Rolex, ensure that the dealer offers a no-questions-asked return policy for a watch that fails to please but is otherwise sound.


Rolex watches often fit differently from each other despite similar appearances and listed case sizes. For new watch buyers, the strong family resemblance between Rolex references – especially steel sports models – can mask vast differences in fit and feel. For example, a Rolex Milgauss (reference 116400) at 40mm has a bracelet whose end-links do not project beyond its lugs, and the wrist-feel is dramatically different from the 42mm Explorer II (reference 216570) with its flared bracelet end-links; the 2mm difference wears like a 10mm disparity on a small wrist! 

Not all bracelets are created equal; Rolex dive watches such as the Submariner and Sea-Dweller families offer immense tool-free length adjustments via special diving clasps built into their bracelets. This is useful for everyday sizing and adjustments in addition to actual diving.

Thickness matters, and it may have more impact on fit than simple case diameter. Rolex models such as the Deepsea Sea-Dweller, Sky-Dweller, and Yacht-Master II can feel huge once test fit to one’s wrist. Although these outlier references are unlikely choices for a first-time luxury watch buyer, any scenario is possible, and inexperienced buyers considering these models must understand how massive they are in the metal.


Finally, a first-time Rolex buyer needs to consider the possibility that he will choose the wrong watch. While it is best to buy with confidence, even the most reasoned choice can be made in error. For this reason, it is advisable for a first-time luxury watch buyer to stick with core Rolex models in stainless steel. 

Steel Rolex “sports watch” references offer the best resale value and the largest permanent marketplace of buyers looking to purchase pre-owned Rolex models. A Rolex GMT-Master II “Pepsi” (126710 BLRO) can be purchased new at $9,700 and re-sold for over twice that if the experience proves unfulfilling. Granted, these days, MSRP purchases entail quite a wait, and used markups are the cost of instant gratification! 

For those with the patience to wait, steel Cosmograph Daytonas, Submariners, and even Oyster Perpetual models are the strongest value-retention plays for neophyte watch buyers who wish to hedge against buyer’s remorse.

Not all new and used Rolex watches entail huge markups or long waits. At the moment, steel-platinum Yacht-Masters, the Air-King, and all Milgauss models are the sportiest Rolex watches that can be bought new without significant delays and at close to retail price when used. Older Datejusts, Yacht-Masters, Oyster Perpetuals, and Air-Kings can be purchased for extremely reasonable prices.

Moreover, a first-time luxury watch buyer with limited knowledge is more likely than an experienced collector to seek reassurances up front, so buying from an authorized dealer of Rolex makes sense. The value of Rolex’s five-year manufacturer warranty and an authorized dealer’s guarantee of authenticity are appealing security blankets for an individual making the leap-of-faith into the world of $5,000+ watches.


Experienced watch collectors seeking to purchase a first Rolex likely fall into two categories. The first is the collector who wants to own an example of an “iconic” Rolex so that the most prominent brand in watches is represented in his collection by a definitive model. The second category of watch-savvy first-time Rolex buyer is the contrarian who may have avoided the Rolex lineup out of aversion to bandwagon mentalities, and this collector often wants to own an offbeat reference from Rolex’s less common model lines.

The experienced watch collector seeking a Rolex “icon” is more sophisticated in taste but similar in goals to the first-time luxury watch buyer. Both should target a steel Rolex from one of the firm’s brand-defining sporting lines. 

Seasoned watch connoisseurs seeking a bedrock model will consider the same references as the newcomers, but a veteran’s specific choice may be informed by other complications, watch classes, and case sizes that already exist in his extended collection of other brands. For example, a collector who already owns a Breitling Navitimer 01 or an Omega Speedmaster Professional may be inclined to complete his collection of iconic chronographs by adding a Rolex Cosmograph Daytona to the mix. 

Or a collector who owns a Blancpain Fifty Fathoms and a Panerai Luminor Submersible PAM 025 may decide that he doesn’t need another dive watch, and his choice might be the GMT-Master II pilot’s watch. Either way, context matters, and an experienced collector should view his first Rolex acquisition as a logical piece of a larger picture.


Many accomplished collectors and connoisseurs of the watch industry spend years avoiding Rolex out of a desire to project independent judgement, counter-culture cool, or simply to express passion for less heralded brands. But many of these anti-Rolex mentalities soften over time, and resentment yields first to grudging respect before mellowing to actual affection. This evolving world view is OK, and often it serves as a starting point for the most interesting class of first-time Rolex purchases.

Those who don’t bleed Rolex green often bring the most independent and unlikely tastes to the table when choosing a first machine from the Geneva giant. It is for these folks that Rolex offers the Milgauss Z-Blue (116400 GV), the quirky Air-King (116900), the big blue Submariner 126619 “Smurf,” and the Cellini line of dress watches. For good measure, experienced collectors often bring larger budgets and willingness to deploy them on watches, so precious metals and serious complications like the Sky-Dweller and Yacht-Master II enter their purchase discussions.

Often, the Rolex hold-out will make a choice that runs against the grain of Rolex history, popular tastes, and high-volume sales trends. This is a win-win for all parties because Rolex gains a client, the Rolex community gains a new believer, a Rolex doubter finds satisfaction, and the diversity of the Rolex product offerings – which is far greater than many acknowledge – is sustained by dollar votes.


Ultimately, the path to Rolex ownership takes many courses. Regardless of the goals that an individual collector chooses, the first step should consist of acknowledging where one’s journey begins. The search for value starts with understanding oneself. What kind of first-time Rolex buyer are you?