On the Road: 10 Stylish Pieces for Motoring Enthusiasts
The designs you need for a life on the road.

It is perhaps the association with travel, or the romance of the open road that gives the nomad's wardrobe its timeless appeal. And it goes back some way. The rise of four-wheeled transport in the early 20th century birthed a number of garments designed to keep the driver comfortable. Early cars were exposed to the elements, so it was important to stay warm and dry behind the wheel. As a result, the car coat emerged in the early 1900s, with its long, duster-style length, and warm wool fabric and button-up front.
But there are other, more contemporary designs linked to the road, both in function and the icons who wore them. The Harrington jacket, for example, wasn’t designed for use behind the wheel, despite its short length and raglan shoulders demonstrating a motoring utility. But variants were favoured by petrolheads, Steve McQueen and James Dean, who would wear them at the helm of a Porsche or Triumph motorcycle.


Speaking of two wheels, biking outerwear has always connoted a certain degree of "cool". Despatch riders in wwII wore long, belted raincoats with slanted side pockets while delivering orders between military units via motorcycle. During this period, Barbour and Belstaff developed their own belted trials jackets, with shorter cuts designed for comfort while seated. Meanwhile, the Schott Perfecto, the classic leather motorcycle jacket, made waves in The Wild One. Upon release, the 1953 outlaw film starring Marlon Brando was banned in the UK for allegedly promoting violence in its portrayal of leather-jacket clad biker gangs.
But what of motoring style today? The good, old classics are still around, but a number of newer brands have emerged with own takes.
"When I started riding a motorcycle in my late twenties, it seemed that the only non-leather jackets being made were variations on the four-pocket trials design," says Ashley Watson, designer and founder of his eponymous brand. "Given that outerwear had followed the same design for decades, I wanted to create a jacket that stood apart. Fast forward eighteen months, seven prototypes, a 4000-mile test trip around Europe, and the Eversholt Jacket was in production."
From riding jackets and motorcycle luggage to driving shoes and chronograph watches, these are the finest pieces designed for a life on the road.


Working directly with the Steve McQueen estate and his grandson, Chase, this striped T-shirt is inspired by a similar style favoured by the late actor and motoring enthusiast. Made in Portugal from heavyweight cotton jersey, it comes with an all-over striped design and would combine well with classic washed denim and suede chukka boots.
Filson Ranger Ranger Short Cruiser jacket
While jackets were essential for driving in the early 20th century, this is no longer the case. But for cooler days or convertible rides, they can still be handy. This Filson Short Cruiser is an ideal outer layer for going behind the wheel. With its hip-length cut, it won’t bunch up when seated, and its lightweight 7oz dry-waxed fabric makes sure you won’t overheat in the sun. Coming with a range of pockets, it’s ideal for holding your passport, or indeed sunglasses, which will easily slot into the buttoned chest pocket.




Bleu de Chauffe Heroes Eclair bag
Handmade in France, this Bleu de Chauffe design offers up an innovative take on the classic leather satchel. Redesigned to double up as a motorcycle saddle bag, it can be worn across the shoulders or attached to the side of your trusty steed. Made from a soft, vegetable tanned, full-grain leather, it comes with an array of pockets, a reinforced back for structure, and solid brass hardware for peace of mind. Ideal for riding or travel, it has a dedicated section for a laptop, so you can arrive at work in two-wheeled style.
Malle London Expedition Duffel bag
Made from a lightweight, waterproof-coated canvas fabric, Malle London’s Expedition Duffel might be the ultimate go-anywhere bag. Its barrel design ensures it can hold a serious amount of kit in its main compartment, from clothes and shoes to a helmet and gloves, while separate zippered sections are ideal for passports, keys, wallets and mementos from the road. A storm flap, sealed seams and zips and a waterproof membrane guarantees it will stay dry inside, while Nato spec webbing allows it to be mounted to the rear of a motorcycle with the included Malle designed G-Hooks.




Ashley Watson Hockliffe jacket
Designed for motorcycling first and foremost, the Hockcliffe jacket comes with a flattering mid-length and handy front pockets, perfect for storing essentials when on the go. But it’s the fabric that’s the key.
"To create the outer shell of the Hockliffe Jacket, we used an innovative ‘core-spun’ technology," says Watson. "The centre of the yarn is made from a combination of Dyneema and Kevlar - which is then tightly wrapped in cotton. This is then woven into a heavyweight twill that has all the characteristics of a heritage workwear. When in hand, you cannot tell that this fabric has a ballistic core."
Silk Road is one of the young brands looking to redefine motorcycle clothing.
"When we set out to create Silk Road, we weren’t interested in repeating the past," says founder Calvin Macleod. "There are already plenty of brands honouring the legacy of motorcycle culture, but we wanted to build something that spoke to the next generation of riders."
These carpenter trousers demonstrate the brand’s intent. They have a classic, regular fit, and are designed to look like regular carpenter pants, with their reinforced knees and hammer loop, but the abrasion-resistant fabric and D30 Ghost armour offers up increased levels of rider safety.




EB Meyrowitz "The Californian" sunglasses
Entirely handmade, E.B Meyrowitz’s sunglasses are among the finest money can buy. This pair is inspired by classic driving sunglasses with their broad width and subtle teardrop shape. Finished in the brand’s Desert Sun colourway, with subtle grey/green lenses, this combination ensures the Californian is an easy to wear pair of shades, whether behind the wheel, or lounging around in the sun.
Taking inspiration from chukka and desert boots, this Connolly pair is designed specifically for driving. Featuring a specially made shank and a non-slip crepe sole, they offer improved flexibility and grip over regular chukka boots, as well as an impressive pedal feel. With their calf-suede uppers and simple three eyelet front, and Italian construction, they’re beautifully made.




Hamilton American Classic Chrono-Matic
Chronographs have long been associated with speed. Whether using one to time laps, measure speed, or just to look cool, this Hamilton Chrono-Matic 50 does the job. Referencing the brand’s own Count-Down GMT Chrono-Matic from the 1970s, with its large barrel-shape case, this updated design adopts a suitably colourful throwback look, its mid-blue dial contrasting with white and orange hands and markers, as well as orange pushers. The perforated racing strap continues the theme, deepening the motorsport connection.
Taking inspiration from classic, 1950s collared leather jackets, the Goldtop 1959 is cut from aniline cowhide, which is beautifully soft while providing the necessary protection for the rider. With a short cut that sits on the hips, it has ball zip cuffs and pockets, a heavy duty Aero centre zip, and soft suede trim inside the cuffs and behind the collar. It also boasts integrated pockets to house elbow, shoulder and back armour. Ideal for wearing astride a vintage motorcycle, but equally stylish for a game of pool at your local roadhouse, it might be the only leather jacket you need.


