10 Driving Shoes That Are Sporty, Sleek, and Stylish

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There are some fashion trends that were birthed in the 1960s, like PVC clothes and go-go boots, that I'm more than happy to let go of. Driving shoes, however, are a '60s style that have gorgeously pervaded decades and remained a timeless staple, evolving in versatility with age—and thank goodness for that.

Back in 1960, the guys who were driving their sleek Italian sports cars had a complaint: those elegant loafers they were wearing were too damn uncomfortable to be putting the pedal to the metal. The solution was driving shoes—a lightweight, flexible, loafer or moccasin-type slip-on made from leather or suede, with grippy rubber-grommet soles designed to keep Ferraris and Lambos steady. Essentially, driving shoes are the sportier, sexier European cousins to loafers—and who wouldn't want to indulge in that?

These days, driving shoes aren't reserved for the act of driving. They're a staple in menswear, worn by everyone from finance bros to Esquire editors to tourists visiting Italy and Italians visiting other countries. Sure, some folks still wear 'em for driving, and nothing is stopping you from doing the same, but if you wanted to wear them into the office with a pair of chinos or to a summer BBQ with a pair of khakis, you wouldn't look even slightly out of place.

Maranello Bow Shoes

With soft leather and suede, these Italian-made driving shoes are an every day staple. With chinos, khakis, or even jeans, you'll look just that much sharper and chicer.

Ayrton Webbing-Trimmed Horsebit Leather Driving Shoes

Driving shoes were invented in Italy, so it makes sense that a luxury Italian brand can carry on the tradition impeccably. Gucci adorns this style with its iconic house emblems, including a monogram logo, horsebit detail, and striped webbing.

Jenson Driving Shoes

Barbour's driving shoes, with contrast stitching and chic lacing, seamlessly merge comfort and style. And if that's not what you want in a shoe, then what is?

Grazioso Embellished Driving Shoes

My father, who has been wearing driving shoes for a good three decades, swears by Ferragamo's. Why? Because the comfort of these shoes is absolutely unparalleled, and the timelessly elegant style is nothing to turn your nose up at either.

City Gommino Leather Driving Shoes

Tod's makes a variety of some of the finest driving shoes out there, but these have to be the best ones. With a distinctly pebbled sole that provides an impeccable grip and smooth, soft leather, there's no going wrong with this subtly elevated option.

Amile Drivers

An American classic. These are simple yet smart, sophisticated yet understated—and isn't that just the Tommy Hilfiger way?

Fletcher Driving Loafers

Sometimes, going the minimalist route is all you need. Nordstrom makes a solid pair of easy, breezy driving shoes for under 100 bucks.

Davis Driving Shoes

For something smart yet simple, turn to G.H. Bass. With contrast stitching, these bright shoes indicate that you should be yachting somewhere on Lake Como.

Dot Sole Roadster Leather Drivers

Of course, if anybody knows luxury, it is Loro Piana. The luxury of these shoes doesn't just come from their high-end leather and quality construction; it's all about the details, too, like an all-around lacing system, rounded toe for comfort, and grippy sole.

The Felize Uomo

Whether you want driving shoes that are bright green, bold orange, or classic black, M.Gemi has you taken care of. These unadorned shoes are comfortable and chic, with a minimalist edge that goes with everything.

Why You Can Trust Esquire

We’re not going to say something is great unless it’s actually great. Every product in Esquire’s round-ups is carefully curated by our fashion and e-commerce teams.

When it comes to driving shoes, you can rest assured that we’re hand-selecting styles that we’ve personally tested, tried, and loved, along with styles that the rest of our stylish colleagues here at Esquire endorse. We’ve had to go through a lot of trial and error, and these driving shoes are the ones that are simply the best.

Every pick on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who and care (possibly too much!) about this sort of stuff, this is the place to be.

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