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How you dress your feet is important. Strangers assess us from head to toe, not head to ankle. That means you’ll be judged by your shoes, and, if we’re being honest, you deserve to be. A well-dressed man is always well-shod. There’s no way around that. Men notice; women notice; the sartorial gods most certainly notice. Why? Because shoes express intention. They declare a worldview, a plan of attack, a sense of who you are. A man who wants to be taken seriously wears serious shoes.

Proper shoes are mostly made in England. Sometimes in America, Italy or, in rare cases, Belgium. They’re crafted with fine leather, often by hand. Some are Goodyear-welted, a century-old technique indicating they’re durable and easily resoled. With attention — regular shining, shoe trees, a wary eye toward heavily salted winter sidewalks — your beloved brogues will last.

Shoes should also be well-proportioned. Please no square toes, one of the few unbreakable rules. Storied companies like Crockett & Jones have used the same molds, or “lasts,” for decades. These are numbered and have their own devotees; I personally enjoy the narrow 314 for tasteful suede oxfords. Alden, America’s great shoemaker, is known for its elegantly rounded toe. You can find them at Leffot, perhaps the best shoe store in the country, which happens to be down the street from my apartment in New York City. It’s worth making the pilgrimage to witness how intense obsession can be; men come here to get custom polish, to put matters in perspective.

Here are 5 footwear options that will instantly establish your credentials on the ground in every room you enter.

5 Shoes Every Man Should Own | Artful Living

Illustration by Hilbrand Bos


It’s good to have a pair of shoes that means business. If they’re lovely lace-ups, then business can also mean pleasure. When it comes to color, I prefer brown. The English have their own theory about the acceptability of blue suits with black shoes, but I believe black shoes are for funerals. Suede oxfords are the ticket with a flannel suit (though by all means wear suede year-round). If you want something more substantial, then a pair of brogues will do — perhaps a burgundy cordovan. Keep a stable of them and take them out for a spin, like your favorite sports car peeling out of your garage. Edward Green and John Lobb are classics for a reason and good places to start.


Loafers are such universally appealing and flattering shoes that I’m surprised more men don’t embrace them. There are as many loafers as there are personalities. Find a style to suit your taste, like a favorite cocktail. There’s something raffish about beaten-up Gucci loafers. There’s something reassuring about Sid Mashburn penny loafers, which look good with everything from cords in winter to shorts come summer. If you’re feeling ornamental, then by all means add tassels, the garnish of the loafer world.

Boat Shoes

You love to spend time sailing at your house on Nantucket. What’s that? You don’t have a sailboat? You don’t have a house on Nantucket? That’s alright — neither do I. But we can look as comfortable as if we did. Sperry boat shoes in blue or brown are very seaworthy, and their white soles won’t mark the deck of your friend’s boat. In a similar vein are camp mocs, the classic brown leather shoes with leather laces, three or four eyelets, and a thin red or brown rubber sole. Rancourt has made them in Maine for ages.

Chelsea Boots

A good pair of boots is practical and stylish. Chelsea boots can be very natty in the English sense. The Beatles wore them with peg-legged suits that were as concise as their shoes. You can still sport them that way if you’re feeling mod. More likely, you’ll don them with jeans or cords, which pair nicely with the versatile R.M. Williams Gardener boot that easily dresses up or down. One thing to keep in mind with Chelsea boots — indeed any shoe — is that their proportion should mirror that of your pants: Narrow boots go well with narrow trousers.


Beloved in certain quarters and misunderstood in others, Belgians are streamlined, lightweight, almost slipper-like, with a tiny bow on top. At first sight, they might seem dainty or dandyish; at second glance, too. But ultimately, they veer to a position of strength. Of those who’ve embraced the Belgian, few go back. The originals come from a small shop on Manhattan’s Upper East Side, but these days you can find variations worldwide. Baudoin & Lange, a wonderful English company, makes a cleaner version sans bow. This is not neutral, which is part of its power. It’s a reminder that the right shoe makes a statement with every step you take. 

A Minnesotan turned New Yorker, David Coggins is the author of the New York Times bestseller Men and Style and writes a style column for Artful Living.

Read this article as it appears in the magazine.

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