Sometimes it can feel that we’re living in an age obsessed with newness. Take, for example, the hoo-ha that erupts every time a certain Californian technology giant unveils its latest (nigh-on identical) mobile device. Or the speed with which certain much-hyped sneakers are debuted, sold out and subsequently forgotten. This is drop culture: a state of frenzied product lust, like Twitter, or Instagram, is predicated upon the idea of very frequent updates concerning things of very little substance.

But it is, of course, not the only reality. Take the following watches, for example. Most of them have been around for decades, one for more than a century. Are they any less compelling now than they were in the distant past? Not at all. In fact, at the core of each of these timepieces is a design that, over the years, has proven too perfect to be seriously tampered with, meaning that the modern incarnations of these classic styles retain the charm and old-world elegance of the originals. As well as proving the worth (and longevity) of a good idea, the lasting appeal of such timeless styles makes each of them a particularly safe bet for anyone looking to take a dive into the world of luxury watches, but not entirely sure where to start. Or, if you’re beginning to put together a collection, something of an icon list to work towards.

In short: you can consider each one of the watches below to be a sure thing.

Find out more at MR PORTER’s Luxury Watch Guide

There are classic military watches, and then there is IWC Schaffhausen’s Mark 11 – a 1948 gamechanger designed for the RAF. The Royal Air Force had demanded: “Watch. Wrist. Waterproof.”  In other words: rugged construction, an inner iron core protecting the precision mechanics from magnetism, decent water resistance, no-nonsense monochrome dial, plus a luminescent triangle at 12 o’clock for quick visual orientation. Mark 11 remained standard-issue for the British military pilots up until the 1980s, and remains IWC’s hero aviator. This year, we’re up to Mark 18, or rather XVIII, and this special edition with steely-blue dial celebrates Mr Antoine de Saint-Exupéry classic 1943 novella Le Petit Prince – IWC being partner of the pioneering 1930s aviator and author’s Youth Foundation.

Shop the IWC Schaffhausen collection here

Mr Louis Cartier’s distinctive rounded-out-square design, which debuted in 1904, was intended for high-altitude japes. Those of Mr Alberto Santos-Dumont in particular. This enterprising Brazilian was notorious for buzzing the lead rooftops of Paris in his aeroplanes. Wrestling the controls had become such a hands-on task that rummaging around for his pocket watch was potentially life-threatening. So, Santos-Dumont consulted his friend, Mr Cartier. The solution was to become arguably the world’s first wrist-worn watch in serial production. In the 115 years since, the curvaceous bezel, its eight exposed screws and gently flowing “shoulders” (both inspired by the neo-industrialism of the Eiffel Tower) were so coherent and beautiful, only a few tweaks and twists have been required since.

Shop the Cartier collection here

What binds all five of our watchmaking icons is that their invention was mothered by necessity. It also helps they’re all masterpieces of utterly coherent, timeless product design. None more so than Jaeger-LeCoultre’s posterboy, the Reverso. Rather than facilitating the smooth passage of an aircraft or racing car, the necessity in this case was an errant mallet smashing your watch dial as you gallop around a polo field. Answering the demand of players during the British Raj, Jaeger-LeCoultre devised an ingenious flappable case, whose sliding hinge allows you to bring the metal caseback to the front, hiding the delicate sapphire crystal. It is so beautifully engineered, with such an addictive “fiddle factor” as to never having required change in almost 90 years. And – more to the point – housed in a beautifully streamlined rectangular design.

**Shop the Jaeger-LeCoultre collection here **

They might be restricted to timing your soft-boiled breakfast egg these days, but back in the 1930s, military pilots’ lives depended on chronograph stopwatches to keep track of fuel reserves. And, from its cockpit instrumentation to the miniaturised instruments ticking beneath their shearling-lined cuffs, the particular brand they depended on was Breitling. The Swiss brand was a pioneer in chronographs from the outset, when Mr Gaston Breitling launched the first-ever push-piece timer in 1915, but it is 1952’s Navitimer that proved indelible – thanks to a feature that’s even more archaic today than wind-up mechanics: a logarithmic slide rule. Rotating about the watch’s circumference and developed alongside the esteemed Aircraft Owners and Pilots Association, it worked in concert with the central chronograph read-out to facilitate on-the-fly calculations, such as airspeed, rate/time of climb/descent, distance, plus conversions between kilometres and nautical mile, gallons and litres. Slide rules have long been dropped from the academic syllabus, but Breitling’s Navitimer still flies high as the choice for commercial and military pilots. 

Shop the Breitling collection here

Much has been written about the seismic cultural changes that gathered pace in 1969, and perhaps nowhere was this better seen than within the watch industry. Precisely 50 years ago, not only did Omega’s Speedmaster reach the Moon, but Seiko launched the very first quartz wristwatch and the self-winding chronograph was finally mastered, twice! First was Zenith, which on 10 January 1969 unveiled its high-frequency El Primero (another contender for this list that just missed the cut). But beating it by a whisker was Heuer and Breitling’s joint effort: the Calibre 11, announced three months later. Powered by a micro-rotor embedded in the mechanics and distinctive for its left-hand setting crown, it first found a home in Heuer’s Monaco. A difficult sell at first, until it became an icon in 1971, when Mr Steve McQueen paired one with a white racing suit and brooding gaze in Le Mans. All Mr McQueen wanted was to dress like his Formula 1 racing hero, Mr Jo Siffert. All Mr Jack Heuer wanted was to sell his Monacos for $220 a pop. By 2012, Mr McQueen’s own Monaco fetched $799,500 at auction. It really is hip to be square.

Shop the TAG Heuer collection here