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No matter how little you know about watches, one thing is universally known and understood: Rolex is king. Culturally, historically, figuratively, hypothetically, literally. It always has been, and it probably always will be. It has the nickname The Crown for a reason, and no one is stealing it from them in a hurry.

 Way back in 1905 when ol’ mate Hans Wildorf was busy founding Rolex, he said he wanted “to be the first in the field”, and for Rolex to “be seen as the one and only – the best.” Amen to that dogged determination and hindsight. Over the almost-120 years that followed, his vision became a reality. Rolex is perhaps the only watch brand you’d expect everyone to have heard of, and a byword for success.

 With that in mind, we figured it worth going through all the best Rolex models and explain what (and who) has helped make each one popular. We asked Brynn Wallner aka Dimepiece, to do the honours. Because, paraphrasing rapper Wiz Khalifa, Time is money, so it’s time to go and buy a Rolex.”

Rolex Oyster Perpetual

The simple, elegant Oyster dates back to 1926 – and might just be the best Rolex ever. It was the first waterproof watch, its name inspired by the tight, sealing properties of an Oyster. A few years later came the term Perpetual, which refers to Rolex’s patented self-winding movement. Conjoined, the term Oyster Perpetual is found across nearly every Rolex dial, indicating that each model is built upon the waterproof Oyster case, fitted with a Perpetual winding automatic movement. But, on its own, the Oyster Perpetual watch is the no-date, steel descendent of the first-ever Oyster.

Got it? OK! With that cleared up, we can discuss the brightly coloured, lacquer dialled OPs that have captivated imaginations and launched a thousand obsessions. Launched in 2020, these trade at least double their retail value and come in flirty hues like candy pink, yellow, coral red… and, of course, Tiffany Blue (not the official name, but we can’t resist). Watch head Kendrick Lamar rocked his (now discontinued, certified grail) 41mm Tiffany Blue OP at the Grammys this year and everyone drooled. To collect each colour is a dream, and capitalising on this, Rolex launched a freshly launched OP “Bubble Dial” dotted with every single colour in the collection. Gotta catch ‘em all!

Rolex Explorer/Explorer II

The Explorer is my favourite Rolex sport watch due to its sheer simplicity. The original reference of this timepiece climbed Everest in 1953, so she doesn’t have to flex extra hard with the visuals – she’s an icon and she knows it. The 3-6-9 (“damn, she fine”) numbers shine against the strong black dial, making for a minimalist statement that would look great styled with your GORP-core or with Levi’s and a pearl necklace. As famed Explorer owner (and Bond writer) Ian Fleming once said, “A gentleman’s choice of timepiece says as much about him as does his Saville Row suit.” So choose what great men (Fleming, Tom Hardy, literal explorers…) have chosen before you. One last thing: I much prefer the 36mm version of this watch, which is better proportioned and more low-key (and less “try-hard”). Less is more, lads.

Rolex GMT-Master II

At its core, the GMT-Master II evokes the fabulous era of flight before long security lines and Crocs were a mainstay. Its predecessor, the GMT-Master, was born out of PanAm’s request for Rolex to create a pilot watch that could keep up with swiftly shifting time zones as commercial air travel became mainstream. In 1955, the GMT-Master debuted, deploying a rotating bezel and a 24-hour hand to display two time zones simultaneously. Then came the improved-upon GMT-Master II in 1983, boasting a better movement and ability to track a third time zone. So, even if you have a smartphone to tell you the difference between GMT, EST and PST, you can set your watch accordingly to subtly flex your LONDON, NEW YORK, LA jetset lifestyle.

 

Now, another thing: if you’re new to the watch world and hear people using nicknames for Rolex watches, they’re often in reference to GMT-Master IIs. The “Coke”, the “Pepsi”, the “Rootbeer”, the “Batman”; these are a few names for GMT-Master IIs per their functional bezel colours that cleverly indicate time of day, e.g. the Pepsi’s colours are red for daytime and blue for nighttime. One last thing, at last year’s Watches & Wonders, Rolex debuted a left-handed GMT Master-II (which has since been nicknamed the “Destro”), shaking the earth under Rolex enthusiast’s feet and claiming wrist real estate on notable lefties like NBA’s Russell Westbrook and West Ham’s Declan Rice. 

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