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.
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.
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.
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.
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.