The enduring appeal of motorsport, especially during its post war heyday, was epitomised by the allure of daredevil racers from legendary race teams, gambling with their lives on the track, and living like there was no tomorrow off of it. This was an era of great glamour and great risk, and perhaps why so many of the ‘classics’ in the menswear canon continue to be drawn from this era. These are the pieces which will inject your look with an adventurous spirit both on and off the track.

CP Company Kan-D “500 Miiglia” Jacket

With its handy pockets for maps and compass, protective hood with integrated goggles, and a sleeve with a single integrated goggle for viewing a watch easily, CP Company’s Mille Miglia jacket was designed by Massimo Osti to be used in the infamous 1000-mile race of the same name. This legendarily dangerous event in which gentleman racers would thrash their vintage sports cars from Brescia to Rome, was also famous for the style of its drivers.

£895, cpcompany.co.uk

Connolly Navy Corduroy Overall

A regulation F1 racing overall is made from fire retardant fabric for obvious reasons and designed with straps on the shoulder so as to be able to lift a driver out of the cockpit easily. The Connolly version, designed with a hidden leather trimmed pocket on the breast for that most important of race essentials – a fine cigar – is an altogether more genteel take on racing overalls than the safety conscious F1 version, and more likely to be spotted in an open top vintage car at Goodwood than at the Grand Prix. It looks just as good in a cocktail lounge, especially if you throw a tailored jacket over the top. Cinch in the waist with the adjustable belt and accessorise with a polka dot scarf and tally ho! You’re off. 

£1,400, connollyengland.com

Persol 714 Steve McQueen

Some sunglasses are simply cooler than others and they don’t get any frostier than the folding Persol 714, the style which Steve McQueen wore in the 1968 film The Thomas Crown Affair in which he played a gentleman art thief and Bullit, The Getaway and Le Mans which all feature fast cars and even racier lifestyles. With hinges at the bridge and temple, the 714 model was the world’s first collapsible sunglasses. The five different coloured lenses offered by the Steve McQueen Special Edition each reference a different period of Mcqueen’s cinematic career: the yellow version pays homage to the Boeing Stearman, the first plane that he piloted, while the blue version are similar to the ones he wore in The Thomas Crown Affair. 

£319, persol.com

Tod’s Gommino Driving Shoes

The classic moccasin driving shoe allowed man and machine to be as one. When they were first introduced 1963, men’s shoes were typically heavy soled and without the nimble, soft construction that allowed them to caress the sensitive pedals of a sports car. Contrary to popular belief it was Car Shoe, not JP Tod’s, who first patented a moccasin shoe with distinctive rubber ‘gommino’ rubber studs on the sole. But it was definitely JP Tod’s, under the leadership of founder Domenico Delle Valle, who made them the global fashion icon that they are today. As stylish in the boardroom with a softly tailored suit as they are in the cockpit of a supercar with jeans, Tod’s Gommino Driving Shoes remain a wardrobe essential.

£450, tods.com

Lock and Co Flat Caps

Motoring used to be a gentlemanly leisure pursuit, not unlike golf. Happily, like golf, it also required its own special outfits and accessories and chief amongst them was the driving cap, which is also known as a flat cap. Slightly less floppy than its cousin the newsboy cap, its sleeker lines also make it smarter than a baseball cap but not as formal as a homburg. They are a specialty of Lock and Co who make summer and winter versions.

From £95, lockhatters.com