Seasons change, and so do styles. One year Air Jordans are all the rage, and the next the comfortable (but hideous) Croc has replaced it. Flip-flops? Depends which direction the wind’s blowing. Tennis shoes? Consider the sport. Boots? You’re in the city now, cowboy. Some looks never go out of style, though, forming the footing for any guy’s wardrobe. Here are four looks—from the tux to the Taylor—guaranteed to put a spring in your step.
A Stroll in the Park
You’ve gotta love Chuck. Forty years after the death of the brand’s namesake, the shoe is still hip—even with punk rockers like Green Day and actors like Entourage’s Adrian Grenier. These low-top Converse Chuck Taylor All Stars are comfy and cool anytime you’re knocking around the house or just going for a stroll. Converse Chuck Taylor All Stars, $39.95. DSW Shoe Warehouse, 8502 Eager, 314-962-8181, dsw.com.
The Black-Tie Affair
A slick outfit requires a slick shoe. Pair a tux with Salvatore Ferragamo Andrea patent lace-ups, and you’ll always be dressed to impress. Made in Italy with leather lining and a padded insole, these European shoes would make even Bond proud. Salvatore Ferragamo Andrea patent lace-ups, $475. Saks Fifth Avenue, Plaza Frontenac, 314-567-9200, saksfifthavenue.com.
A Night Out
So you’re meeting friends for drinks, and you need a shoe that stands at the crossroads of business and casual. You want something that says “confidence”—but isn’t too outlandish. Not for the faint of heart, the Air Donovan Chelsea dresses up any look and protects your feet from puddles (of rain or beer) during a night on the town. Air Donovan Chelsea boots, $248. Cole Haan, Plaza Frontenac, 314-997-3460, colehaan.com.
Another Day at the Office
The shoe for any office worker—classic brown, sleek but masculine. These leather beauts can slip on while you’re grabbing a cup of coffee, and the removable OrthoLite footbed makes the 8-to-5 grind a bit more bearable. Umberto Raffini’s Cesare loafers, $159.95. The Walking Company, The Meadows at Lake Saint Louis, 10 Meadows Circle Drive, Suite 102, 636-561-3325, thewalkingcompany.com.