Ah, the iconic driving shoe. What was once synonymous with the jet set, vintage automobile enthusiasts, and Mediterranean excursions has taken on a new resonance, given our renewed interest in the All-American road trip. Today’s best men’s driving shoes still have their original mid-century features — moccasin silhouettes made with premium fabrics and rubber-grommet soles for superior pedal grip and traction — along with some modern flourishes that make them the perfect off-duty shoe. And now that we’re all spending more time in our cars, their utility lasts well past summer. Here are some of our favorites.
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Best Driving Shoe Overall: Cole Haan Somerset Bit Loafer — $110
In terms of value, quality, and comfort, Cole Haan’s driving shoes stand above the rest. Rendered in a tasteful, low-luster-sheen leather, these versatile loafers feature a soft-yet-sturdy cushion and a classic silhouette that will look and feel great for years to come.
Best Luxury Driving Shoe: Salvatore Ferragamo Stuart Driving Shoe — $530
Salvatore Ferragamo’s storied driving shoe is a favorite among petrolheads and bon vivants for countless reasons. Among them: They’re made of supple Italian leather (swoon), they slip on like butter, and they elevate just about any outfit. If you can afford them, they’re well worth the sticker shock.
Best Budget Driving Shoe: Florsheim Sportster Moc Toe Penny Driver — $80
You don’t necessarily have to splurge a car payment for a fashionable pair of Penny Drivers. Take these ones from Florsheim, which contain a memory foam cushion that will keep your toes stylish and cozy for even the longest car rides.
Best Suede Driving Shoe: M. Gemi The Felize Suede Moccasin — $198
Yes, European sportscar drivers of yore wore leather, but a suede driver shoe is a bit more versatile, as it can dress down, or dress up, almost any outfit. You can’t go wrong with these moccasins from M. Gemi, a handmade shoe brand that’s grown a cult following over the years.
Most Comfortable Driving Shoe: Ugg Henrick Twinsole Driving Shoe —$70
Surprise! Your mother’s favorite aughts boots make some seriously comfy driving shoes, thanks to its cloud-like footbed that’s also moisture wicking.
Best Leather Driving Shoe: Tod’s Gommino Full-Grain Leather Driving Shoes — $575
We have to include Tod’s, one of the OG labels who put the driving shoe on the map (or the road, rather). The brand’s bottoms are dotted with 133 rubber pebbles for maximum grip, and their tops — made in gorgeous tan leather — aren’t so bad, either.
Best Cotton Driving Shoe: Ted Baker Cotton Driving Shoe — $150
A cotton finish and contrast stitching add a trendy twist on the classic, and we love the results.
Other Driving Shoes We Love
To Boot New York Driving Shoe — $295
Fitted with a suede upper, leather lining, and an arch-support footbed, there’s a lot to love with these slip-ons.
Aurelien Light Blue Suede Driving Shoes — $196
Made for leisure and luxury, these Ultramarine driving shoes are thoughtfully designed for comfort every step of the way.
Wolf and Shepherd Gunner Driver — $198
These sleek gratin leather slip-ons are made with memory foam and extra cushioning, so they literally feel like slippers, and they come in seven different colors.
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