By Mason Maynard

The Essential Casual Shoe (and Other Ways to Dress Down)

In the 119 years since Sigmund Florsheim started making shoes in his tiny Chicago workshop, the world has seen the rise of cross-trainers, flip-flops, Crocs, and those webbed-toe abominations that let you walk and run as if barefoot. And yet for all this progress, a man still needs at least one pair of casual shoes that look like something ol’ Siggy might’ve cobbled himself. Something with a beefy sole and some firm support in the arch. Something durable that can take both a polish and a beating. And, most important, something with some personality to it. The brand that Florsheim built is still in business and enjoying a creative revival, led by the forward-thinking fifth-generation members of the Florsheim family, and these gray, personality-packed leather wing tips from its new heritage-driven Limited line are just the extra 10 percent that any casual look could use.

Here are a few different styles that can be tried out. One way is the right way to wear them, the other are my suggestions on how to switch it up. I also add what you could wear with each pair!

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Moccasins: The Right Way

The most casual shoe this side of sneakers.

Choose a simple pair in dark leather and lose the socks for maximum comfort. Since you’re playing it safe with your shoes, feel free to turn up the volume with your pants.

Moccasins: My Suggestion

Travel outside your color comfort zone with a sky-blue or bright-red moccasin. Keep your pants a muted shade and let your shoes do all the talking.

Ankle Boots: The Right Way

Not those tough, mountain-ready SOBs that have been so ubiquitous these past few winters. We mean the soft-handed, easygoing ones that are right for spring.

You’ll pair your standard-issue beige boots with blue jeans and you’ll look great.

Ankle Boots: My Suggestion

You’ll pick a pair in an unexpected color, with a contrasting-colored sole, and you’ll wear them with dark casual pants. You’ll look better.

Bucks: The Right Way

The classic round-toed, red-rubber-soled casual shoe for spring and summer.

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White and clean, with muted khakis or even a pair of rumpled seersucker trousers. Socks are optional.
Bucks: My Suggestion

Look for variations on the classic buck like Zegna’s, which loses the laces altogether and bleeds the red of the rubber sole onto the toe cap. Pair them with an equally unexpected color of pants and throw in some go-to-hell socks while you’re at it.

Wing Tips: The Right Way

Come Saturday, leave your dressy, thin-soled, delicately brogued wing tips in the closet and opt for their more casual cousin; the brogueing will be a little more pronounced, the sole a little thicker, and the toe a little rounder.

Ditch the socks and try a pair of lightly colored suede wing tips that contrast with a pair of bold pants.

Wing Tips: My Suggestion

Choose a brown leather pair with a bright-red sole, keep ’em polished, and wear them with striped socks and dark-blue jeans.

The Sneaker Hall of Fame

If you’re going to wear sneakers with jeans or trousers, go classic.

  • New Balance 999
  • Spring Court G2
  • Converse Jack Purcell (My personal favorites)
  • Vans Classic Slip-On
  • Converse Chuck Taylor All Star


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Plus: Note to Self

Swap out your standard-issue shoelaces for a pair of brightly colored laces. They add personality to everyday lace-ups.