Wearing a Rolex makes you feel like you’re a part of something—the lore, the history, the objectively iconic design. Like the NFL’s #12 jersey, many great men have worn Rolex. It’s why the crown connotes a rarified tier of luxury. But the barrier to entry is actually lower than you’d imagine. There are surprisingly approachable ways to discover the brand.
A Rolex Sub under three, four, or even five thousand dollars? Impossible. But clubs have back doors. Systems are hackable. And there are two cheat codes that few people know when entering the Rolex market: defunct vintages (often visual ancestors to current icons) and unique, forgotten designs. These are two perfectly respectable, totally legit, non-exorbitant ways to join the league.
These conversation pieces often flaunt the defining characteristics and stories we turn to Rolex for. Vintage wrist wear supplies humility, personality, and charm. Besides, the biggest name of all isn’t Explorer or even Submariner. It’s Rolex.
See more vintage: We hunted down Hollywood’s most famous mystery watches.
Rolex Royal
The Rolex Royal: Fundamentally Rolex
Aesthetically, the understated Royal sits somewhere between the sportier Oyster Perpetual and the dressier Day-Date. It’s also a low-key icon. I’m just waiting for the day a major influencer namechecks it, inflating its market. Until then, it’s one of few vintage Rolex sublines under $5,000, sometimes as low as $1,000.
It debuted in 1933, going against the grain with its central second hand instead of a subdial. Transitional designs are highly coveted, especially ones that represent an industry shift still relevant today.
Thanks to decades of production, you’ll find several iterations of the Royal. If you love the Arabic cardinals of the Explorer, search for references 6244, 6044, 6246, or 6144. For the version Cary Grant may have worn in Charade, check out the double-baton cardinal version of the 6244 or the 4444.
My favorite Royals are the 1950s 6444s. The crown application is placed directly above the handset instead of as the 12 marker. It also comes with an engine-turned bezel, which looks like a fluted bezel, but less ceremonial and more industrial. I’m simply compelled by this balance of familiarity and peculiarity.
Rolex Marconi
The Rolex Marconi: Different Is In
With the Rolex 1908’s 2023 release, I have a feeling that un-Rolex-like Rolexes will pique people’s curiosity. For those who think such Rolexes don’t exist, I introduce you to the defunct Marconi. Its existence is mostly scrubbed from official histories, likely because many of its designs don’t perfectly fit the current mold. Rolex likes to brand itself as consistent and never changing.
Once Rolex’s premier line and sold only to select clientele, Marconi watches sometimes sell for less than $1,000 today. The line boasts different colors, shapes, and motifs, all running on the Marconi manual wind. If you dig deep, you’ll find some Marconi Primas with the 1908’s Breguet-like hour hand. Marconis are affordable because they aren’t auction-house darlings. But who knows? Perhaps the 1908 will breathe new life into the market.
Rolex Oyster and Oysterdate Precision
The Rolex Oyster and Oysterdate Precision: The OP’s Pinch Hitter
There’s a small part of me that wonders why there are so many round-ups for affordable luxury alternatives to the Rolex Oyster Perpetual when the Oyster Precision exists. Certainly, vintage isn’t always convenient, but it has a cool factor. And Rolex watches are built to last. Though they’re dressier than the OP, core Oyster Precisions feature several hallmarks, including the Oyster case, baton indices, and the crown 12 marker. Oysterdate Precisions have an added date function.
Basically, they represent the blueprint from which all Rolex watches are built. Oyster Precisions are also the last manual wind Rolexes ever made, so they check the box for interesting history, too. Black-dial 6694s look like the vintage Submariner’s dressier cousin. I’ve even seen a few 6694s and 6426s with the iconic Mercedes hands.
Buy an Oysterdate Precision on 1stDibs
Buy an Oyster Precision on 1stDibs
Rolex Cocktail Watch
Want Something Distinct? Try a Rolex Cocktail Watch
Snaking gold bracelets, Deco-esque twists and turns, and feuille handsets—doesn’t sound very Rolex, does it? Search for “Rolex cocktail watch” in any secondary market. You’ll be amazed at how many ornate and unique models Rolex seems to want you to forget. Again, it’s likely an attempt to brand itself as steadfast and anti-trend.
Imagine the satisfaction: A friend looks at your watch and asks if it’s vintage Bulgari. You discerningly say, “Rolex, actually.” The cocktail watch has all but disappeared in the annals of time, especially in menswear. However, as we continue to leave the bigger-is-better era, I hope and pray for a cocktail comeback. Most vintage and antique cocktail models are labeled as ladies’ watches because sellers think women are more likely to buy them. However, cocktail watches are historically unisex.
Rolex Air-Kings
Vintage Rolex Air-Kings: Connecting Vintage and Contemporary
And, of course, there’s always vintage Air-Kings. Since the latest 126900 is actively on the Rolex roster, there’s something a little less throwback about going this route. The Air-King continues to hold down the fort as the crown’s long-time entry-level model.
You might find the COSC-certified reference 11420 in and around the $5,000 mark. It’s exceedingly rare, but crazier things have happened. In my opinion, the sweet spot is the generation from the ’90s and aughts, featuring five-digit references. The 14000 is as elegant as a modern OP, sunray dial and all. Or, you can get the version with the large Explorer-esque cardinals.
My favorite? The 14010. Its now-discontinued engine-turned bezel just looks so distinguished. Both the 14000 and the 14010 can easily be found for under $4,000. If there’s an M at the end of the reference, it means it’s an upgraded version with a more precise movement. Meanwhile, second generation models—reference 5500 and 5700—can go as low as $2,500.
