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The Six Driving Shoes to Consider

  • Kempt Staff


It wouldn’t be Road Trip Week if we didn’t talk about the most important part of your road-worthy wardrobe: the driving shoe.

They come in many forms—some are more loafer-like, some are more moccasin-y—but they’re all united by two things: a buttery-soft leather construction and gummy rubber bottom (marked by a telltale matrix of nubs embedded in a double-thick leather sole).

They’re especially handy on a breezy weekend jaunt, because they’re handsome enough to wear to cocktail hour yet soft enough to loaf around indoors, once you’ve woken up the next morning at your destination. Meaning they’re the only pair of shoes you’ll need to pack if you’re not planning on anything too formal or a round of golf.

Naturally, we’ve rounded up your six best options on the market right now.»

Pennies for Your Thoughts

  • Najib Benouar

via Cool Hunting

The more advanced footwear enthusiasts have been swapping out their laces for something more colorful for some time now, but for the loaferly-inclined, there wasn’t much you could do to punch things up.

Luckily, Benjo’s—the folks partly responsible for the brightly waxed lace revolution—have come up with a solution. Color-coated pennies. We’ll wait for a moment while your mind returns from being blown. Okay, you’ve got plenty of colors to choose from—N.B. Greenberg calls out to us, mostly by name—so don’t be afraid to get bold (this is why you opted for penny loafers in the first place).

And in case you don’t already have a pair, let us remind you of these Allen Edmonds we mentioned yesterday.

Stepping into Autumn

  • Najib Benouar

It would be remiss of us not to alert you to a handsome new batch of Allen Edmonds shoes that have just landed at UrbanDaddy Perks. It’s the first place you’ll be able to get your hands on AE’s newest cognac-hued line of shoes (there’s a couple wingtips and a loafer), made in Wisconsin—at an equally good-looking price. This is how you’ll kick your fall wardrobe into high gear.

Summer on the Crepe

  • Najib Benouar

The crepe sole penny loafer has been quietly gaining traction since they popped up on Yuketen’s Americana-phile shoe rack a few years ago. They’re a bit quirky on first glance, but for anyone who’s enjoyed a crepe-soled bounce in their step, it’s well worth a few wrinkled noses.

This new pair from Oak Street Bootmakers (one of five new designs that have just hit their webshop) is the best-looking incarnation we’ve seen yet. It’s got the heritage-approved beefroll stitching (that extra leather from the top strap that rolls over the toe stitch) and Horween Chromexcel leather. And it’s all handcrafted in the USA.

Most importantly, you can give your desert boots a rest till fall.

Summer of Vintage Love

  • Najib Benouar

The vintage shop beat can be more trouble than it’s worth if you’re not looking in the right places.

One of our favorite places to look: the Brooklyn-based Wooden Sleepers. And they’ve just replenished their stock (both dead and vintage) on Etsy—just in time for your summer weekending to come. It’s a kaleidoscope of vintage anoraks, tassel loafers and brass bookends, so we thought we’d help you wade through the well-curated bins with a look at some of their best new offerings after the jump.

Let’s get vintage-ing, shall we?»

A Little Memorial Day Encouragement

  • Najib Benouar

Memorial Day means many things to many people. To all Americans, it’s a day to celebrate those who put themselves in harm’s way to protect this great land. And to most sartorial traditionalists, it marks the first day we are officially allowed to wear white shoes.

It’s a tricky move, especially when you’re trying to incorporate them into a more formal look. (Otherwise, grab a pair of white canvas sneakers and beat the hell out of ’em.) Herewith, your answer: these white suede loafers from Alden. They’re so pristine, you might shudder at just the thought of them touching city pavement, but with great risk comes great reward.

This will be the summer you learn to stop worrying and love the white suede.

Possibly the Most Italian Shoe We’ve Ever Seen

  • Najib Benouar

Tassel loafers and driving shoes have been getting a lot of love this season—each with their own merits—but this best-of-both-worlds hybrid from the Tuscan cobblers at Arfango is a horse of a different color. You’ve got the suede, unstructured slouchy comfort of the driving shoe paired with the formal finish of a tassel loafer. It’s what you’ll want to be wearing the next time you find yourself tagging along for a semiformal soiree on the Amalfi Coast.

As it typically goes with releases of this nature—midseason, by a lesser-known overseas label—finding a pair of these is going to take a little work (or an Italian translator). So aside from hunting down a proxy, your best bet is to wait for them to wash up stateside—we’d suggest keeping an eye on Barneys, who carry Arfango, but have yet to stock this particular model. Happy hunting.

The Summer Loafer

When summer rolls around, we usually jump pretty fast for cotton sneakers, but there are plenty of other options—and a few of them put your plimsolls to shame.

This one comes from Osborn Design, with cotton uppers and leather soles. The result lands somewhere between a weejun and an espadrille—the kind of thing you’d wear to a semi-formal beach party. It’s also one of the most discreet ways to pull off that loose, sockless, “I’m-almost-barefoot” vibe that tends to surface in July.

Just keep the foot powder handy.