Long ago, at the dawn of the automobile age, whole fashion categories sprang up around the novel pastime of motoring. Certain staples from that era survive vestigially, their original utilitarian purpose lost to obscurity. You can still find a duster, for example—a loose, lightweight, ankle-grazing coat devised at the turn of the past century to protect clothing from the dirt kicked up by horseless carriages. Also still among us are low-crown, brimless motoring caps, built to withstand wind blasts.
Persisting from later, midcentury car culture are the car coat, cropped to a three-quarter length to avoid bunching up on the driver’s seat, and the driving shoe, thin-soled for flexibility, cleated for traction, and patented by the Italian cobbler Gianni Mostile in 1963.
Accoutrements that, for better or worse, have become obsolete include goggles with amber lenses and strapped leather helmets, such as the rakish one that Tamara de Lempicka wears in her 1929 Self-Portrait (Tamara in a Green Bugatti). The billowing muffler framing her face was at that time a hazardous accessory. Just two years earlier, Isadora Duncan, as The New York Times noted, “met a tragic death at Nice” when her long, fluttering, painted-silk scarf got stuck in a spoked wheel of her lover’s Amilcar CGSS and broke her neck.
Among the kinkier appurtenances advertised for early male and female automotive enthusiasts were glossy black-kid knickers and leather puttees. Small wonder that Marcel Proust fell in love with his chauffeur, who, the writer recalled, draped himself “in a huge rubber mantle” and “wore a sort of hood which fitted tightly around his youthful beardless face and which, as we sped faster and faster into the night, made him look like some pilgrim, or rather, a speed-loving nun.”
I, too, am a speed-lover, but only when someone else is driving. A Connecticut state trooper once pulled me over for going too slowly on I-95. But like Proust’s chauffeur, I have always given careful thought to what I wear inside a fast vehicle. I remember well the modish madras kerchief I tied under my chin as a little girl whenever my father took me out for a ride in his rear-engine red convertible.
Today, in a performance convertible like my friend Joe’s Python Green 2021 Porsche 718 Boxster GTS 4.0 (more on Joe later), I would probably protect my hair with a 90s Gene Meyer chiffon scarf, knotted securely at the back. For eyewear, I’d gravitate to Jacques Marie Mage’s black Slade cat-eyes, fierce-looking enough to subdue an aggressor’s road rage. The rest of the outfit would consist of my default warm-weather travel ensemble—a gray or blue Thom Browne seersucker trouser suit paired with his sturdy pebble-grain loafers. The abbreviated jacket’s interior pockets are ideal for stashing those small loose objects—pens, lipstick, AirPods—that tend to go missing in a car.
In an enclosed luxury sedan, like a Bentley Flying Spur Mulliner, or a rugged S.U.V., like a Mercedes G wagon (both available on turo.com), I might switch to an Alaïa moto jacket and knit dress, or an Edeline Lee Polydora sheath, cut from a wrinkle-proof techno fabric. If the dress is color-coordinated with the car, so much the better. Either way, I’d finish the look, in cooler weather, with Uniqlo Heattech tights, flat Manolo booties, and a hard-frame, jumbo Mr. Thom bag, stuffed with almost any item you might find in a drugstore. Though a lap rug was once de rigueur—both Eleanor Lambert and Diana Vreeland kept cozy with leopard throws—I do not furnish a car’s interior with anything more extravagant than a needlepoint cushion, for lower-back support.
For male attire, I defer to Joe, car collector and creator of the “Car Crush” show on YouTube and the most dapper gearhead I know. Joe advocates layers—a Brunello Cucinelli zip-front cardigan topped with a reversible calfskin jacket, “maybe with a hood,” a silk-and-cashmere-blend Loro Piana scarf, and “a dash of Etro,” probably in the form of jeans. For footwear, Joe prefers Tod’s sneakers or driving moccasins, and for shades, Ray-Ban aviators.
“The watch,” Joe notes, “depends on the car.” To complement his green Boxster he likes a “Jaeger-LeCoultre Compressor, with a big dial, quite technical-looking. You can tell the time from a distance. Every second counts when going fast!” And for tooling around in his two-door 1967 Rolls-Royce Silver Shadow, he leans “toward a Cartier Tank Américaine. It’s virtually impossible to tell the time due to the tiny white-gold hands—and isn’t that really the point when you’re driving an old Rolls?”
Unlike the lady motorists of yore who would decorously replace their disheveled garments before reaching their destination, Joe believes that looking freshly windblown upon arrival is the ideal finishing touch for any stylish driver.
Amy Fine Collins is an Editor at Large at AIR MAIL. She is the author of The International Best-Dressed List: The Official Story
