‘Cool’. One of those prevalent words that loses all meaning and starts to sound weird if you say (or type) it over and over again. But we say it all day every day, sure in the knowledge of its meaning – an X-factor that transcends all other positive qualities to denote that intangible, seemingly effortless, hip-to-the-game… well, cool.

As the ‘Cool Wall’ of Clarkson-era Top Gear proved, when it comes to high-end products, no amount of technical trickery, marketing or inflated pricing can guarantee coolness. A picture of a Fiat 500 sticks happily alongside an Aston Martin DBS, united in their respective cool. Meanwhile, the Lotus Exige S is shamed into the ‘Uncool’ portion of the board, next to a Nissan Micra.

And so it goes with cool watches, which – if we’re honest – are just like cars: status symbols with an everyday purpose, often unnecessarily overengineered, increasingly anachronistic, and all-too-often the unwitting broadcaster of less-than-fortunate ‘qualities’.

They also bestow much enjoyment to their owner, so you could argue that if you love your watch, who gives a damn what others think?

Well, we do. And as our (wholly subjective of course) shortlist demonstrates, it needn’t cost the earth to guarantee a cool watch game. Mostly thanks to the importance of restrained design and minimal bells or whistles. A proven heritage helps too, eliciting ‘if you know, you know’ kudos from the watch world’s inner sanctum.

Luckily, watchmakers are wise to this, explaining why so many classic models have remained in production for decades, virtually unchanged. It also explains the recent explosion of vintage reissues, bolstered by the unflagging trend for retro.

Of course, you’ll have your own ideas of what constitutes a cool watch – so do please let us know. Sure, maybe we’ll disagree. But, you know, that’s cool.

Tudor Heritage Chrono

Don’t let Tudor’s relationship to mothership Rolex distract you – this is a brand furrowing its own path with recently renewed vim and vigour, especially when it comes to a nostalgic take on the manly tool watch. It’s by no means affected however; its Heritage Black Bay diving watches stem from decades of endorsement by the French and US Navys’ elite combat divers.

But two years before the Tudor Black Bay’s revival, there was the Heritage Chrono of 2010 – a groovy update of a seventies cool cat, straight off the boat at Monaco’s quayside. Coming on either a striped nylon ‘NATO’ strap or a stainless steel bracelet, this is a seriously smooth chronograph with state-of-the-art engineering to boot.

Buy Now: £3,160.00

Rolex Sea-Dweller ref. 126600

Most will know of James Bond’s original watch of choice, the Rolex Submariner – still just about the most complete watch you’d ever want. It arose with the boom in recreational SCUBA after the war, but by 1967, the hardcore commercial divers of France’s Compagnie Maritime d’Expertises (COMEX) needed to take things up (or rather, down) a few levels.

Rolex’s response was the Sea-Dweller Submariner model – upped from 300 to 610m water resistance (nowadays water-tight to a scary 1,200m) and fitted with a helium escape valve for drawn-out ‘saturation’ dives. What’s all-important to Rolex aficionados, though? That scarlet-red dial text, as per the original – catnip to collectors, with a just-enough whiff of danger.

Buy Now: £8,700.00

Bell & Ross BR 01-92

Since the mid-nineties, the crisp monochrome utility of Paris-based (but Swiss-made) Bell & Ross has earned it as much love among turtlenecked architects as bomb disposal squads or naval pilots. And it’s the latter that provided the inspiration for 2007’s bombshell: the uncompromisingly massive (like, 46mm massive), uncompromisingly square ‘Instrument’, complete with corner screws, just like the dials in a fighter jet’s cockpit.

There have been puns on that very theme, with ‘Compass’ and ‘Altimeter’ models. You can now even squeeze it under your cuff in 42mm ‘BR 03’ guise. But the original ‘BR 01’ is still Maverick to Bell & Ross’s Goose.

Buy Now: £2,800.00

Omega Speedmaster Professional

It might not boast the most alternative looks, or even the most progressive mechanics, but that’s the point: that’s why the Omega Speedmaster was the only chronograph to survive NASA’s brutal tests back in the sixties and earn a watch-brand marketeer’s Holy Grail of approval: qualification to officially ‘fly’ on the wrists of astronauts, as standard-issue kit.

Precisely 50 years ago, it was a Speedie strapped to Buzz Aldrin’s spacesuit as he stepped out of the Eagle onto the Lunar surface, earning its eternal ‘Moonwatch’ nickname, and it’s still keeping time aboard the ISS. As the last man to walk on the Moon, Gene Cernan attests, “the Speedmaster Professional chronographs remained virtually unchanged throughout the entire Apollo program – no other piece of mission-qualified equipment can make that claim.” You want cool? You could stop reading here and now.

Buy Now: £3,680.00

G-Shock DW-5600E-1VER

We all know rappers like their bling, but surprisingly it can manifest in resin rather than gold – specifically in the form of a G-Shock, the cult statement wear for all manner of hip-hop artists, fashionistas, surfers, plus the majority of the world’s special-ops military men.

This seminal hardman was conceived in the same year as our other plastic-fantastic cool cat, the Swatch – but while the Swiss were pioneering precision injection moulding, the Japanese were striving to pass their own self-conceived ‘triple 10’ test: water resistance to 10 bar (about 100m), a 10-year battery life, and most importantly, the ability to survive a 10 metre drop onto a hard surface, unscathed and working perfectly.

There are now myriad iterations, blessed with all manner of GPS and Bluetooth wizardry, but as always it’s the purest version that remains most faithful and, yes, the coolest.

Buy Now: £100.00

Longines Legend Diver

Full disclosure: the author wears one of these. And it’s the original no-date-window model first re-released in 2007, to boot, now long-discontinued. Which means, just by typing that, any hopeful cool factor has been rendered moot. Pay no mind, just get yourself the slightly unfaithful date version and rock the vintage reissue that kickstarted the whole vintage reissue craze in the first place.

The ‘patinated’ off-white numerals complement neutral tones beautifully and it’s still a bona fide sub-aqua instrument, with a crucial point of difference to the usual diver format: an internal rotating bezel, adjustable with the screwed-down crown at 2 o’clock.

Buy Now: £1,640.00

Swatch Twice Again

We’ve all owned one, but did you ever know your plucky Swatch watch is nothing less than the watch that, back in the eighties, saved the Swiss luxury watch industry from the onslaught of cheap Far Eastern quartz technology? Which is ironic of course, being that it is a cheap quartz watch.

It was invented almost by accident, when an engineer at Switzerland’s one-stop-shop for movements, ETA, recklessly spent 500,000 francs on an injection-moulding machine in the same year the firm had made 4,000 staff redundant. When his manager found out, he had just two hours to come up with a proposal: a cheap quartz watch that used ultrasonic welding to build the mechanism straight into the case. No screws, watertight, with just 51 parts, and little else to go wrong. Nothing has changed since in principal, and it’s still as fun but also discerningly democratic as it’s ever been.

Buy Now: £50.00

Hamilton Khaki Field Mechanical

Before joining Switzerland’s vast Swatch Group as über-affordable cousin to stablemates Omega, Longines et al., Hamilton was one of America’s biggest watchmakers – making it the default choice for US infantry during World War II. This millimetre-perfect reissue is as faithful as it gets to its forties forebear, equipped with a historically correct manual-wind movement.

Continuing the modern-day Hamilton’s reputation for bafflingly good value, the price tag makes it even more irresistible. Complete the look by driving a camo’ed-up 1940s Willys Jeep – arguably cooler than a Mk1 Land Rover, and pair with selvedge denim and a cotton chore jacket for ultimate rugged workwear points.

Buy Now: £395.00

TAG Heuer Monaco Calibre 12

The year 1969 was a big one: not only did NASA and Seiko respectively take Omega’s Speedmaster to the Moon and quartz technology to the market, but the self-winding chronograph was finally realised – twice. Arguably, the post was pipped by Zenith and its immortal El Primero, but Heuer (along with Breitling and Büren) was the first to industrialise its own “world-first” automatic stopwatch, the Calibre 11 sooner.

It found its first home in the Monaco – an avant-garde combination of out-there squareness and far-out mechanics, and it now houses the Calibre 12 – a specially adapted ETA base with a Dubois-Depraz chrono’ module. Still as ice-cool as when Steve McQueen donned his in Le Mans, and still every petrolhead’s “grail watch”.

Buy Now: £4,350.00

Seiko Prospex ‘Orange Monster’ Diver

Finally, in 2015, the fully-equipped giant of Japanese watch brands Seiko responded to European watch nerds and relaunched its cult, US- and Asia-only “Orange Monster” diving watch into the core collection, only under a new name, “Prospex”.

Its automatic movement isn’t anywhere near the Swiss-rivalling standards of the Grand Seiko imprint, but who cares about losing or gaining a few minutes a week – just look at it: rock-solid utility with just-don’t-give-a-darn ‘Tuna Can’ proportions at a startlingly low price point. Oh, and that startlingly garish dial, of course. Roll up your sleeve and dare casual observers not to say anything.

Buy Now: £950.52

Nomos Glashütte Metro Date Power Reserve

This is a watch running the risk of being uncool by virtue of its cooler-than-school USPs. But everything, from the Bauhaus design codes to the in-house-crafted mechanics ticking inside, has irrefutable integrity and elegance. In Germany’s historic hub of fine watchmaking, Glashütte, Nomos was the first ‘proper’ watchmaker to lift a pair of tweezers with the fall of the Berlin Wall.

But with typical humility, it soon knew that designer ‘edge’ doesn’t progress in remote, mountainous Saxony. Hence the establishment of Nomos’s design studio at ground zero for cool: east Berlin. Here, its unique modernism is painstakingly evolved at the hands of creative sorts with angular haircuts, fuelled by artisan coffee and avocado on rye.

Buy Now: £2,980.00

Patek Philippe Nautilus ref. 5711

The word ‘cool’ is rarely linked to Geneva’s grande maison of all things exclusive and expensive, steadily nurturing its legacy of refined, hand-crafted dress watches, packaged up in tasteful shades of eggshell and claret. But in the seventies, the luxury sports watch arrived, much to the benefit of the otherwise-stuffy realms of top-end Swiss watchmaking. Arguably it’s all down to one man too, Gérald Genta.

Having designed the previously unthinkable with 1972’s still-iconic Audemars Piguet Royal Oak, he effected the same revolutionary thinking at Patek Phillipe. Like the Royal Oak, the Nautilus had a rounded octagonal shape and ‘integrated’ bracelet, and like the Royal Oak it’s still virtually un-tweaked, with even more power to summon the heady extravagance of the disco era.

Buy Now: £22,820.00

Panerai Radiomir Base Logo

Today, Panerai is an established Swiss watchmaker – a jewel in the crown of the Richemont Group – but this former Florentine naval-equipment manufacturer was in the doldrums as recently as 1995, when an unlikely and decidedly un-cool personality played a critical role in its revival. Sylvester Stallone was shooting Daylight in Rome, where he spotted a Panerai Luminor in a jewellers’ window and went on to order a batch for his friends – Arnie included. Word got out and by 1997, Richemont had bought the brand.

The purest of its line-up, named after Panerai’s innovative luminescent paint, draws from the first diving watches made for the Italian Navy’s frogmen in the thirties, sub-contracted to Rolex. The cushion case contours to a slender, rounded-out square, with only the easy-to-grip conical crown and wire lugs interfering with an otherwise perfectly smooth ‘pebble’ of steel. Tales of derring-do, under-the-radar celeb endorsement and gorgeous on the wrist. That’s cool, right?

Buy Now: £3,400.00