The Rules of Wearing Driving Shoes

By Megan Gustashaw

Driving shoes—leather or suede moccasins with rubber-grommet soles—were invented for men who wanted extra grip while driving seriously gorgeous Italian roadsters. Seventy-odd years later, they've been adopted by investment-banker hotshots, Italian style heroes, and loads of other bros who don't technically hold a title to a Ferrari. Which is perfectly okay. Times change. The only thing you don't want to do, if you're into the look yourself, is treat them like hard-bottom dress shoes, wearing them everywhere from the office to nightclubs—especially with pants that are too long for their own good. Here's a recap of how to do the driving shoe right.

The Car Shoe suede driving shoes, $335, available at carshoe.com

The driving moc is meant to be a little bold—but don't automatically reach for the first flashy orange pair you see. We're into rich jewel-tone colors or strong neutrals that are free of high-contrast stitching.

Tod's Gommino driving shoes, $495, available at mrporter.com

This isn't a set-in-stone thing, but we're partial to driving shoes worn without socks (or at least with the invisible variety). The flash of ankle will add to the casual vibe the shoes provide, making you feel like a guy who's never had to deal with a 9-to-5.

Tom Ford Samuel suede driving shoes, $690, available at mrporter.com

You don't need a gorgeous Italian car to wear driving shoes, but you should use their leisure origins as a cue for when to wear them in 2016. Think: lunch with friends or a movie date, not a client dinner or a wedding.

Jack Erwin Parker driving loafer, $115, available at jackerwin.com

Slim (not skinny) jeans or chinos that don't have much of a break at the hem are the ideal choice. Nice cotton shorts work as well. If you want to dress up, a suit that's cut slim and in a casual fabric like cotton or chambray will look great, but don't take that as permission to wear the driving shoe at formal events.

M. Gemi Veloce driving shoes, $198, available at mgemi.com

No man who owns a luxury car would wear his driving shoes until the nubs are worn off and the toe is dirty. Even if you don't own such a vehicle, you should take the rich guy's lead and keep them pristine.