Where the runway meets the street

We teeter with our attitude toward dressing up. Too few men bring dedication and creativity to how they pull it together, but putting on a three-piece suit and leather-soled shoes every morning is extraneous. Where shoes are concerned in the quest for a well-curated shield, there are fine lines to walk. It all depends on the spikiness of the hair or his overall Kanye-ness, for instance, but sometimes a dude in a suit wearing high-tops looks like a real dick.

Find the right casual shoe for gussying with, however, and you are a comfortable killer.

A selection of shoes we might pair with fancy pants and blazers after the jump.

FeitHand-sewn Superclean High

This high-top night horse comes with a leather sole, making it the closest thing on the list to an actual dress shoe. Cut and hand-sewn by a single craftsman in Australia China and ready to look understated but bold with a suit—especially if you roll the pants some. For total refinement: the shoe is soft to the touch, biodegradable and ages like wine.

ClarksOriginal Wallabee

Walter White wears these, so you are not so much filling the shoes as borrowing them.

Creative Recreation – Lacava Sneaker

These have the visual pop of a wild high-top with a much lower profile. Pants could interact in interesting ways with the heel tab. Hidden laces suggest that you are solid and keep important things in-pocket—good for a first meeting (hyperbole).

Gravis – Buxton

There are a handful of fake-out dress shoes on the market now, but we are drawn to the Buxton from Gravis. Having worn pairs of their Reider loafers and Oxblood Dylan slip-ons into the ground (both put up one hell of a fight), we feel confident that the construction is solid. Soles are rubber and supposedly skateboard ready, though they do have a heel.

Shoes Like PotteryKiln-Baked Canvas Sneakers

The Hunter Thompson we hold inside us was screeching to include some white low-top Chuck Taylors, but we are a little tired of dressed up Cons. How about some dressed up Shoes Like Pottery instead? These are baked in a kiln, which would have intrigued the Good Doctor, no doubt.

Paul SmithRipley Boat Shoe

Figured we owe you a boat shoe. This one is nice because it’s upper throws in the curve-ball fringe of an insurance salesman’s loafer.

Birkenstock – Zurich

99.9 percent of the sandals on the planet make us want to toss it, and that’s not even counting the millions upon millions of flip-flops we are forced to endure the sight of as soon as 50-degree weather arrives. So we are very surprised to be including Birkenstocks on this list. Blame Waris Ahluwalia. Dude makes them look refined as a mother-effer with a light-colored suit, and has probably given us the false confidence that they will work for us. Not comfortable biting his steeze directly, we bring you the Zurich, which covers a little more foot and, thus, makes us a little more comfortable.

Emerica – Wino

Here’s another skate lifestyle shoe, because our impulse to wear sneakers even while dressed up stems from youth, when wearing skate shoes at all waking hours sent out a signal that you were indeed a skateboarder. These are an excellent mimic of those wino shoes you see shuffling about on the feet of grizzled day drunks. Don’t they look dashing in seer sucker?


There is still a little bit of ’90s Compton hardness-envy buzzing about in our psyches like a cluster of hornets and the only thing that will quiet the riot is the Cortez. You could wear these with some crisp work pants and a lumberjack flannel under your blazer for extra authenticity.

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