The right pair of shoes
Footwear is an essential part of dressing well, but it’s often overlooked. Far too often a good outfit is ruined by a bad pair of shoes (or a great pair of shoes is wasted on a crappy outfit). A well-dressed man will have a solid rotation of shoes that will complement every outfit in his wardrobe, whether they make a statement on their own or act as a quiet anchor. To help you find a few pairs that look good and suit your style, I’ve put together some dos and don’ts and a guide to a few different types of footwear, as well as illustrations of a few of my favorite shoes in my “collection.”
It’s not hip to be square. Except for the occasional pair of Clark’s Wallabies, square-toed shoes are one of the greatest footwear sins, especially on dress shoes and loafers, which is where they’re most commonly found. Instead, opt for a more natural round toe that’s not too flat but also not pointy. Save those for the elves.
Less is more. It’s cliché, but shoes should be fairly simple. You don’t need shoes with 20 different colors and a bunch of bells and whistles — colors should be complementary and any straps, zippers, et al. should be functional. It’s okay to have a standout pair of shoes, but make sure they don’t venture into garish territory. For example, a pair of suede oxford bucks with a neon sole or a pair of bright blue sneakers can be great, but rainbow Air Force 1s are probably a bit too much.
Save your flip-flops for the beach. No one wants to see your gross, hairy feet. And for God’s sake, don’t wear them in winter. (You know who you are.)
You can never go wrong with classics. There are tons of great new styles cropping up, but there’s a reason shoes like Jack Purcells are still going strong.
What to buy: A few examples
Everyone should have a couple pairs of casual shoes that aren’t sneakers. Desert boots, which were originally British military boots, are my favorites — the J.Crew Macalister and the Clark’s Original Desert Boot are the most popular choices. Try sandy brown suede, brown leather, or a colorful suede like navy or green with a gummy crepe sole. Then there’s the Ivy staple — the penny loafer. Try a rich brown from Bass for an affordable start. Or, opt for a pair of driving mocs from Minnetonka for something more casual. Suede bucks also make a great option, with a classic red or playful neon sole.
To me, the essential dress shoe will always be a wingtip brogue (broguing refers to the small perforation detailing in the leather). I like mine to have the slightest bit of heft in the sole, but there’s a place for thin and sleek as well. There’s also the classic cap toe, which has a piece of leather sewn over the toe, as well as the more rakish monkstrap — both double and single. Pick two styles, one in black and one in brown, and you’ll be set. Try Allen Edmonds, Brooks Brothers, J.Crew, Macy’s, and Alden (my favorite) for starters. Make an investment now and they’ll last forever.
Here’s where you can more easily inject your personal style into the mix. There are endless styles to suit every personality. Some great classics are Adidas Gazelles or Stan Smiths, Converse Jack Purcells, Nike Killshot 2s or Air Force 1s, New Balance 574s, and Vans Classic lace-ups or slip-ons. For something more modern, try Nike Roshe Runs or Frees or Common Projects (I’ll admit I’m not as well-versed in newer sneakers). You can’t go wrong with white, black, and navy, but a skilled eye can pick out colorful sneakers that work just as well.
Every New Yorker needs a pair of warm, waterproof boots for the winter months. A pair of Sorel 1964s or L.L. Bean “Bean Boots” will serve this purpose well. For something more suited to autumn, Red Wing 875s or Iron Rangers or Chippewa Service Boots are some of my favorites. Pick something rugged like these and they’ll only look better over the decades that they’ll last you.
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