Amid a crowded field, the GMT-Master and its successor, the GMT-Master II, might just be the most desirable family of Rolex models right now. The Daytona will always command a higher price and other references are rarer, but there is something zeitgeisty about the GMT-Master. Its use of colour is part of it, as is the way it bridges, particularly in vintage form, the world of tool watches with something a little bit dressier. This ref 1675 is about as pure an example as you could wish for, with strong, well-preserved original colour on the aluminium GMT bezel insert and uniform faded tritium lume across the dial and handset.

The Rolex Explorer celebrates its platinum jubilee this year, having entered the world in 1953. In its seven decades, it has become one of the most popular and widely collected Rolexes and is an ever-present by which you can chart the history of the brand. This example, from the turn of the millennium, is an early reference 114270 with calibre 3130, applied numerals and the famous Mercedes hands that have been present on almost every Explorer. With this Rolex, you are getting a modern, reliable, no-nonsense timepiece with a connection to the glory days of watchmaking.

The Explorer is so fundamental to Rolex that when the time eventually came to introduce an upgraded successor, it felt no need to discontinue the original Explorer. The Explorer II adds a number of features that you might genuinely use in the wild, chief among them a 24-hour fixed bezel and GMT hand (which can, at a pinch, help you navigate by the sun). It is bigger, chunkier and more overtly tool-ish, but has barely changed in the past 30 years, as evidenced by the condition and timeless functionality of this 1987 example.

The Day-Date 36mm in yellow gold is quite possibly the original status watch. Not in the sense that no one before ever used a watch to signal their wealth and importance – 18th-century pocket watches were quite the flex – but in the sense that it was the first wristwatch to achieve a kind of totemic presence that surpassed its (relatively modest) mechanical abilities. The weight of gold, the shimmering cut of the fluted bezel and the simple, verging on farcical literalism of the name all combine to make it a true archetype, loved by high-status men from President Lyndon B Johnson to Mr Michael Jordan.

For a brand so closely associated with in-house watchmaking (it even smelts its own gold, such is its commitment to controlling every step of a watch’s production), it is curious that Rolex didn’t have its own automatic chronograph movement until 2000, when it released the Daytona 116500 series with calibre 4130 inside, a thoroughly modern chronograph movement with a 72-hour power reserve. The white dial, stainless steel ref 116520 was, and remains, one of the most popular Daytona references of the era.

Few recent Rolex launches have attracted as much debate as the Air-King. This version was replaced in 2022 by a model that “fixed” some small details, such as the case shape and polished 3-6-9 numerals. But, just as the new reference has its fans, no sooner was it changed than some people expressed a strong preference for the outgoing model. There’s nothing like a discontinued Rolex – which was in production for only six years – to get collectors twitching.

Rolexes can be brash. As the most famous watch brand in the world, it is not difficult to understand why they are often bought as status symbols by those eager to be noticed. But they can also be subtle and restrained, like this 1996 Oyster Perpetual. At 34mm across, it is the perfect size for everyday use (don’t listen to anyone who says it’s too small, at least until you’ve tried it) and with its simple baton markers and slimline hands against a plain black dial, it gives you just what you need, no more and no less.

If there is such a thing as a sleeper in the category of Rolex sports watches, the Yacht-Master could be it. Physically and conceptually close to the Submariner, it has managed to carve out a different character despite sharing the same dimensions and movement. Its lesser water resistance reflects its position above the waves rather than beneath them, but 100m is ample for even the most adventurous sailor. This reference 126622 stands out for its colourful dial – something you will never find on a Sub – and ghostly platinum bezel.