Rolex Sky-Dweller
Unlike many of the watches listed in this article, the Rolex Sky-Dweller hasn’t been around for decades. In fact, it’s only been around for one! Released in 2012, the Sky-Dweller nevertheless boasts technical prowess and style, which can only be the result of over a century’s worth of Rolex R&D. Here, the Sky-Dweller name is not used to describe a pilot, but rather a world traveller. The ‘50s produced GMT-Masters for pilots; but in 2012… Think about it. Pilots had computers for in-flight timekeeping, and any watch on the wrist is purely ornamental. So, the Sky-Dweller was built for modern travel, featuring a complex dial that, however busy it may be, conveys an intuitive dual time-zone. Rolex was perhaps having a bit of fun when they developed this watch, riding high off the flashy y2k energy that preceded its release.
The y2k vibe can also explain its size, which clocks in at a hulking 42mm – en vogue at the time, and rather bulky compared to the smaller-leaning, vintage inspired trend we’re currently exploring. And yet despite its humble lifespan and high millimetre count, the Sky-Dweller remains a status symbol for those brave enough to rock it. Tom Cruise wears one, as does Jack Harlow. Then there’s Michael Jordan and LeBron James, who both wear it proudly. If it’s good enough for the GOATs…
Rolex Air-King
The first commercially available Rolex Air-King debuted in 1958, hot off the heels of the GMT-Master. These were the glory days of smoking cigarettes in first class PanAm seats. But the original Air-King came about during the 1930s “Golden Age of Flight”, when pilots were honing aircraft engineering and commercial flight existed only in their imaginations. The original Air-King featured enlarged 3, 6 and 9 numerals (much like the Rolex Explorer), rendering its dial legible mid-flight, but was far simpler in build than the GMT-Master. Now, celebrating its 65th year, the Air-King has undergone several evolutions; but you may recognise the name from its association with the now certified-grail Domino’s Pizza Rolex.
These are simply Air-Kings customised with the Domino’s logo, gifted to top earners within the company. During the time, somewhere in the ‘80s and ‘90s, the Air-King was known as a ‘starter Rolex’ with an $800 price tag, and yet this was enough to incentivise employees. Now, these Domino’s Air-Kings are sought after amongst a whimsically-minded type of collector and have skyrocketed in value on the secondary market, trading for as high as $19K. That’s a lot of dough!
Rolex 1908
If you’ve made it this far in this article, you may have noticed a pattern – most of these heavy-hitter pieces are tool watches – built for sport, built for industry, built real tough. The Day-Dates and the Datejusts might look good with a suit, but you may find yourself asking ‘What if I want a proper dress watch?’ The discontinued (and underrated) Rolex Cellini is a good option – but the Crown has another proposal: the vintage-inspired Rolex Perpetual 1908, which debuted at Watches & Wonders in 2023 and was quickly snapped up by Roger Federer. Named for the year Hans Wilsdorf registered the Rolex trademark in Switzerland, the Perpetual 1908 checks all the dress watch boxes (classy, time-only, precious metal, leather-strapped) with the bells and whistles of modern Rolex (namely the exhibition caseback that shows off the ultra slim, very efficient automatic calibre 7140 movement). At £19,300, the 1908 provides good value for collectors looking to class up their repertoire – and for those of us not willing to drop tens of thousands of dollars, the 1908 should provide good inspo to dig into Rolex’s discontinued dress watches. You’d be surprised at the sheer variety that falls under the Cellini line, ranging from simple leather-strapped offerings to wild, jewellery-forward pieces apt for the brave standing proudly in opposition to the “stealth wealth” trend.