This handsome classic has been a PF Flyers icon and stylish silhouette for nearly a century—and shows no sign of stopping anytime soon. This version of the Center Lo is a modernized take on the original. Since 1937, when the brand debuted the first insole designed specifically for sport shoes, P.F. Flyers have found a unique balance between form and function. You'll find that these are more comfortable than your average canvas kicks, thanks in part to a slightly wider toe box and a cushy Ortholite foam footbed offering long-term support and moisture management.

The J.Crew design team actually spotted this shoe in one of their catalogs from the '80s and decided to remake it, with a few updates so it feels decidedly 2023. Crafted from durable leather that will take on your wear patterns and look even better over time, it's got a single monk strap (for a toned down look) and a thick lug sole that not only feels fresh, but adds a nice bit of comfort as well.

Red Wing has long made handsome, quality work boots that are built to last. If there was a downside to buying a pair, it was that they tended to be ruggedly weighty and required some time to break them in. But the brand's take on an old-school chukka boot offers a much lighter and casual take. Crafted from an oiled and waxed nubuck leather with a flexible (and resoleable) stitch-down sole, they're designed to give instant comfort right out of the box without sacrificing any of the brand's signature craftsmanship. These could be the last chukkas you ever have to buy.