In the mood to go for a drive? Cruising along on the open road has got to be one of the best feelings in the world. You’ve got your snacks in the passenger seat, your favorite podcasts and playlists ready to play and a mapped route or no directions at all in search of your destination. Driving can be a daily chore you do to get from point A to point B, or it can be a grand adventure, a celebration of the mind-blowing innovation that is a combustion engine on four wheels that moves us to exactly where we need to be. The next time you take a drive, we commend you don’t just do it in any old pair of men’s boots or loafers for men — but in men’s driving shoes instead.
What are driving shoes? Well, they’re basically loafers but with a few key differences. They’re one of the fanciest, classiest and occasionally snottiest men’s fashion trends out there that’ll make you feel like you’ve time traveled back to old Hollywood. I mean really, a loafer specifically for driving? It doesn’t get more Casablanca than that. Next you’re going to tell me there are specific hats made for playing chess, or watches made for diving. Hang on, that last one is actually a thing. Regardless, driving shoes are loafers made of high-quality suede or leather that typically have a thick sole with plenty of traction for gripping the pedal. No slipping with a pair of these babies on, plus you’ll look extra classy. There’s no fancy vehicle required to rock a pair of these — so pick your favorite and don’t forget to let Jeeves the butler know you’re heading out.
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1. Calvin Klein Men’s Karns Driving Loafers
BEST OVERALL
If you’re new to the driving shoes trend this pair from Calvin Klein is just bougie enough without going overboard, and is neutral enough to match a variety of outfits. They’ve got a Moc-toe and a slip-on design for comfort, a padded tongue and flexible sole. The leather body is classic and they’re available in black and brown so you’ve got choices design-wise.
2. Cole Haan Men’s Gunnison Driver
RUNNER UP
These driving shoes have more of a classic moccasin construction that’s hand-stitched with antique brass eyelets for added flair. The rawhide laces tied out front add a slipper aspect to this loop but the flexible rubber sole has a heel protector so you’ll be able to fully grip the pedal. The leather upper is also smooth, shiny and can be dressed up or down depending on the occasion.
3. Andes Driving Shoe
BEST DESIGN
The best men’s driving shoe have the classic loafer feel with a little design flair here and there. These shoes from BØRN are a great example, with contrast stitching and tough, thick full-grain leather. The sole is textured for a firm, dependable grip on the pedals and the simple overlay up top adds a distinctive look to these simple slip-ons.
4. Tommy Hilfiger Men’s Dathan Driving Style Loafer
BEST BUDGET
You don’t need to fork over an arm and a leg for a classy pair of shoes these days — and these classy Tommy Hilfiger slip-ons are testament to that. They’ve got a thick synthetic sole and moc-toe stitching that’s quintessential driving shoe. The embossed logo on the tongue adds a nice tough and the foot bed has light cushioning to keep your feet comfortable during long hours on the road.
5. Sperry Men’s Gold Cup Harpswell 1-Eye Driver
BEST TRACTION
A key element of a good driving shoe is the traction. These driving loafers from Sperry have deep grooves in the sole that give you the traction you need to handle any machine, and they look super stylish up top as well. The full-length cushioned footbed molds to your foot throughout the day so you stay comfortable and the lambskin linings give your foot a soft surface to rest in. These shoes also have Anti-Shock and Vibration technology in them, perhaps from their sea-faring makers, that give them an extra boost above the competition.
6. Bermuda Driving Loafer
MOST COMFORTABLE
All driving shoes are designed for comfort, but these Bermuda loafers have a squared moc that won’t squish your toes and a driving sole that’s segmented and wraps around your heel for a secure fit. The soft leather upper will cradle your foot in comfort and the thick sole will protect it from rough ground below.
7. Parigi Bit Driving Moccasin
BEST SPLURGE
One of the premiere designers who makes driving shoes is Salvatore Ferragamo — apparently he loves cruising as much as we do. These loafers from him have excellent reviews, contrasting stitching, brushed silver tops and a metallic, industrial ornament that makes the predictable look unique.
8. Cole Haan Wyatt Penny Driving Loafer
BEST SUEDE
Aside from leather, suede is the other popular fabric for driving shoes due to it being a soft, comfortable fabric that’s also a little chic. These Cole Haan driving shoes have a suede upper with a vamp crafted for breathability and style. They have a cushioned footbed for comfort and a rubber outsole pod for traction and extra padding. They come in a few light and dark colors, but I love the British Tan for all seasons and looks.
9. Leather Driving Moccasins
BEST LEATHER
If you’re gonna go bougie driving shoes, Brooks Brothers might be the brand to trust with the look. These leather moccasins have the classic driving shoe design with a preppy “penny catcher strap” on the vamp. The leather is Italian calfskin crafted from some of the best shoe craftsmen in Italy. They have a soft construction for foot flexibility, a rounded toe, a cushioned insole and pebbled sole for grip.
10. Lucien Driving Shoe
BEST STATEMENT SHOE
If you’re going to wear driving shoes, you might as well make a statement out of it right? These driving shoes from Sandro Moscoloni are just bright enough to stand out in any room or setting. The contrast stitching adds to the design even more and evokes a classic Spanish driving loafer. They’re made of supple, soft suede and have smooth leather overlays with bright laces as the final touch.