5 All-Time Great Classic Cars & The Watches To Drive Them With

When we first started putting together ‘In Good Company’ back in 2022 there was a part of me that felt overly concerned with the notion of resisting cliché.

Still, as astute observers have figured since the days of Isaac Newton, it’s impossible to fight gravity forever; which is why this October’s edition of the column is dedicated to arguably that most obvious of watch-related pairings - iconic automobiles.

The connection between luxury watches and cars can feel very overbaked in 2023; but there are genuine reasons as to why the two pursuits have tended to orbit one another going all the way back to the early 20th century. Beyond the innately mechanical nature of both inventions, watches have been an organic element in car manufacturing and car culture for decades.

There’s also the dynamic connection between watch brands and historic motorsports (once practical instruments; now symbols of status) or, more recently, the proliferation of material science that is as salient to carmaking as it is watch manufacture.

Point being: there are a lot of car-inspired crossovers we could consider for ‘In Good Company’; though, this October, we thought we’d start things off nice and intuitively with a look at 5 ‘classic’ cars and what we daydream about having on our wrists behind the wheel.

All created at least half a century ago - and thus, closely aligned with the popular definition of a ‘classic’ automobile - each has had a seismic effect on motoring enthusiasts and the way that we conceive of sports cars.

Ferrari 250 GTO (1962)

Hailed by Hagerty’s Colin Comer as “the last of the true dual purpose road & race cars”, the Ferrari 250 GTO is the final incarnation of the vaunted 250 series.

Initially produced as a homologation special - for induction into the FIA’s Group 3 ‘Grand Touring Car’ category - Ferrari made the 250 GTO in staggeringly small numbers. By the time production ceased in 1964, just 36 examples had been produced.

This in turn has contributed to the record-breaking performance of the 250 GTO at auction: until last year, it was the most expensive car ever publicly sold; with one example at Sotheby’s fetching as much as $48.4 million back in 2018.

Wear It With: Richard Mille RM011 Chronograph ‘Felipe Massa’

For a car that combines desirability, performance and a legacy of competitional excellence (over 300 racing victories) in such explosive fashion; the watchmaking of Richard Mille is a no-brainer. To really emphasize the ‘Prancing Horse’ connection, it’s hard to do much better than this RM011-FM.

A cutting-edge chronograph in titanium - combining Richard Mille’s signature flyback functionality with a large date and even a month display - it is a fitting tribute to the Brazilian F1 driver Felipe Massa - most noted for his career with Scuderia Ferrari between 2006-2013.

Jaguar E-Type (1961)

Widely revered as the most beautiful car ever made (Enzo Ferrari was reportedly a fan) Jaguar’s Series 1 E-Type has the enviable quality of being the aesthetic benchmark against which every two-seat sports car must contend in the last 60 years.
 

A real driver’s favorite that has aged shockingly well, the E-Type is still capable of reaching top speeds of 150mph and acquits itself effectively in the handling department - thanks to its then-groundbreaking combo of independent rear suspension and disc brakes (mechanical features still in use today).

Wear It With: Rolex Daytona Ref. 6263 ‘Sultan Of Oman’

More than all things technical however, motoring enthusiasts love the E-Type for its looks. Malcolm Sayer’s distinctive elongated frontal bodywork imbued the car with an aerodynamic silhouette that appears almost fluid: an elegant canvas upon which to subsume smaller details such as the distinctive flared in headlight or  ‘clamshell’ bonnet.

Timeless and very nearly divinely proportioned, this bodywork evoked a reaction in us similar to what you’ll find in the Rolex Ref. 6263 Daytona - more specifically, this version commissioned by the Sultanate of Oman. Unveiled by Rolex a decade after the E-Type’s inception, you needn’t dig very deep to gather why each is an icon of its field.

Among Daytona lovers, the 6263 has a reputation for being among the most visually balanced executions of this classic chronograph one can own. As a bonus: the ‘Sultan of Oman’ models possess - much like a Jaguar - a uniquely British connection, being pieces commissioned exclusively from the London retailer Asprey under the Sultan’s royal warrant.

Porsche 911 Carrera RS 2.7 (1972)

Considered to be a “genre-defining” moment for Porsche’s already crazy-iconic 911 lineage (six decades old and still going strong) the RS 2.7 figures prominently in the minds of classic Carrera collectors all over the globe.

Another product of European racing’s homologation rules, the RS 2.7 brought with it a host of innovations that had never before been seen in a road-legal 911. This model was the first to be constructed with the iconic ‘ducktail’ spoiler, enlarged rear wheel arches and the now-universally recognized ‘Carrera’ lettering - inspired by the mythically dangerous Mexican road race of the same name.

With all the above came new heights of performance: at the time of its introduction, the RS 2.7 was the fastest production car ever to come out of Germany. Thanks to innovative weight reduction solutions and relentless honing of the engine’s fuel capacity (up 0.7 litres, hence the ‘2.7’ moniker) the RS 2.7 was able to reach speeds of 100km in 5.8 seconds - blistering fast even today.

Wear It With: A. Lange & Sӧhne Datograph ‘Up/Down’

Obviously, the pride of Stuttgart deserves a timepiece that’s similarly competition-busting; and so, for this pairing, we turned to A. Lange & Sӧhne - the final word in Saxonian high watchmaking.

The brand’s 41mm Datograph - much like the RS 2.7, a radical technical improvement on an existent design - allows precise measurement of speed and increments of up to 30 minutes; whilst packing in a number of other informational displays (e.g. the ‘outsize date’) that have since become integral to the brand’s identity.

Mercedes-Benz 300 SL ‘Gullwing’ (1954)

A serialized version of the historic ‘W194’ racing car, Mercedes-Benz introduces its distinctive gullwinged coupé in 1954. The project possesses a unique connection to the post-war boom of the American market, where importer Maximilian Hoffman advocated assiduously for “a great Mercedes-Benz sports car”. Thankfully, the bigwigs at Daimler-Benz were listening.

Going from concept to unveiling in a record-short five months, the ‘W198’ Gullwing was the first passenger car to be equipped with direct fuel injection. In conjunction with the appropriately futuristic sounding ‘spaceframe’, the 300 SL lived up to Mercedes-Benz’s goal of creating an extremely light, high-performing sports car.

Possibly one of the greatest vehicular examples of the maxim that ‘forms follows function’, the 300 SL’s iconic upswinging doors were in fact a by-product of efficient engineering. The spaceframe chassis’s extra sill height proved incompatible with conventional doors - so Mercedes-Benz engineers solved the problem by again borrowing from the exterior of the W194.

Wear It With: IWC Big Pilot Perpetual Calendar ‘Antoine de Saint Exupéry’

While an IWC chronograph designed in partnership with Mercedes AMG would seem like the obvious match for the 300 SL (in both personality and performance), we’ve opted for a different tact by going with this ‘Big Pilot’ perpetual calendar.

Inspired by the French aviator Antoine de Saint-Exupéry, this particularly complicated riff on the ‘Big Pilot’ works extremely well in the context of long-distance driving. Legibility is excellent across the board and the in-house calibre 52610 will run unassisted for a whole 7 days.

One might also contend that Kurt Klaus’s integrated perpetual calendar module (in which every single indication is set with the winding crown) reflects the traditional engineering prowess of the 300 SL’s 250hp engine.

Aston Martin DB4 (1958)

The precursor to the car that would be immortalized in pop culture through the 1964 James Bond adventure Goldfinger, the DB4 is ultimately responsible for seeding the DNA of Aston Martin’s most iconic and universally beloved grand tourer. A mere glance at details such as the swept rear end and distinctive side vents tell of a shared lineage.

For historians of British car manufacturing, there’s a lot to love beyond the obvious throughline between the tail-end of the DB4 series (including special variations such as the GT Zagato) and the DB5.

The DB4 was the first grand tourer to be wholly built at Aston Martin’s new factory in Newport Pagnell; while its body was built using an innovative construction known as the Superleggera - a framework of steel tubes reinforced with aluminium panels, allowing for greater freedom in the creation of innovative body shapes.

Wear It With: OMEGA Seamaster Diver 300M ‘No Time To Die’

That isn’t to say that the high esteem collectors hold the DB4 in rests solely in its dashing looks. When it was initially introduced at the London Motor Show in 1958, the DB4 caused an immediate sensation with a roaring straight-6 engine - designed by the racer/engineer Tadeusz Marek - capable of reaching 100mph in less than 30 seconds.

For a car of this nature - rare, “transcendently handsome” and still more than capable of cutting it in the 4,000rpm rev range - we’d be remiss if we didn’t at least suggest one of Omega’s Bond-inspired Seamasters. The No Time To Die edition (which Bond actor Daniel Craig actually had a hand in designing) possesses the same rugged but unfussy handsomeness that is the DB4’s calling card.