MR PORTER looks back to a time when men knew how to hit the road in style.

There is more to being well dressed than just the clothes. It’s about the life as well as the wardrobe, and a man’s method of transport is an important element of the stylish life. Here at MR PORTER we’re promiscuous when it comes to transportation: we’re big fans of cycling and we’re certainly not above public transport, but we also love driving. It’s undoubtedly easier to make a good impression if you emerge from the cabin of an Italian coupé, rather than from an underground station, and if you’re offering someone a lift home after dinner, it’s more tempting if she knows that you’ve got the keys to an Aston in your pocket, rather than the keys to a D-lock. This is something the men in these photographs knew well, and they set an almost unbeatable benchmark when it comes to automotive style.

Ferrari 250 GT

It’s hard to imagine how any man, regardless of his clothes, could look bad in a Ferrari 250 GT, but it’s just as hard to think how a man could look any cooler at the wheel than French actor Mr Jean-Paul Belmondo, dressed in a suit and tie. Note that not even an icon of France’s legendary, ennui-filled New Wave movies cannot resist grinning like a Cheshire cat.

Jaguar E-Type

Mr Frank Sinatra was the best-dressed member of the Rat Pack, but Mr Dean Martin clearly had much better taste in cars – Ol’ Blue Eyes’ last car was a Chrysler LeBaron station wagon. Jaguar’s famous 150mph E-Type is one of the great 1960s sports cars, and arguably the most beautiful, but, unlike most, it’s relatively affordable today. Driving a convertible E-Type is surely the chicest way to get a tan.

Ford Thunderbird

Looking at this photograph of Mr Arthur Miller nonchalantly driving his Ford Thunderbird, with his wife Ms Marilyn Monroe in the passenger seat, it’s hard to remember that he was a playwright, rather than a playboy. There’s little about his car’s extravagant lines, or his wife’s extraordinary curves, that you’d associate with a bookish personality. The only visual clues are his wool sweater and casual shirt.

Ferrari 250 GT Lusso

These days, Mr James Coburn, a Hollywood tough guy who notably appeared in Mr Sam Peckinpah’s 1977 film Cross of Iron, is remembered as much for his cars as for his acting. He famously owned a 250 GT California, a car that British radio DJ Mr Chris Evans bought for more than £5 million in 2008, as well as this beautiful V12 Lusso, which was designed by Pininfarina, the celebrated Italian design house.

Porsche 550 Spyder

This Porsche, which is as handsome as its driver, is a racing version of the marque’s four-cylinder, 1.5L 356 road car, which was what Mr James Dean drove until he bought this 550 in September 1955. The car deserves to be remembered for its fabulous good looks, and its class-winning success in the 1,865-mile-long Mexican Carrera Panamericana road race, but these facts are inevitably overshadowed by Mr Dean’s fatal accident in the 550 on 30 September 1955.

Triumph TR3

The appeal of most French exports, things such as red Bordeaux wine, steak tartare, Ms Laetitia Casta and the classic Citroën DS, is apparent. The appeal of the singer Mr Johnny Hallyday, however, remains largely mysterious beyond his country’s borders, but that takes nothing away from his appearance in a soft-shouldered jacket behind the wheel of a TR3, with the Arc de Triomphe in the background.

Morgan Plus 8 Roadster

Sir Mick Jagger’s choice of car – a hand-built English sports car with an ash-wood frame that’s made in rural Worcestershire – reinforces his British image, even if this photograph was taken in the south of France. This shot is from 1971, when few people could have predicted that 44 years later The Rolling Stones would still be touring, and that, just as astonishingly, Morgan’s convertible would still be in production.

Cadillac Eldorado

When the actor Mr Richard Burton met the actress Dame Elizabeth Taylor on the set of the 1963 film Cleopatra, he reportedly declared that he’d sleep with her within 48 hours. In the end, it’s said that five days passed before they consummated their famous relationship. And the reason we’re rehearsing this cheap celebrity gossip? They are said to have first made love together on the back seat of Mr Burton’s Cadillac.

Jaguar XKSS

Mr Steve McQueen was famously interested in guy stuff – he’s said to have turned down a date with Ms Ali MacGraw in order to stay at home and wax his Belstaff jacket. While he’s most closely associated with the Ford Mustang he drove in Bullitt, he chose to drive this British racing-green XKSS, a bizarrely proportioned, road-going version of Jaguar’s legendary Le Mans-winning D-Type.