Sorel Derby LTR Shoes
Sorel purportedly took inspiration from “European armies of the mid-1800s.” We’re not sure what that means, but we can tell this low-key, all-leather shoe has impressive mojo. Though it’s not as cushioned as other models here, the Derby’s grippy rubber traction made us think, as we sprinted to catch a train, that we were wearing a minimalist runner.
Rockport Eastern Standard Casual Mid PT Shoes
The pinstriped lining initially drew us to this chukka-desert-boot hybrid. But it was the supreme comfiness of the Adiprene cushioning in the heel—the same stuff you find in Adidas’s top-of-the-line shoes—that kept us coming back. A siped-rubber sole ups the grip on slick surfaces.
Scarpa Manhattan Shoes
These stylish sneakers are understated enough to go where others wouldn’t dare to tread, yet they still announce to the world that you’re a mountain type. Of all the lifestyle sneakers we’ve worn over the years, none has been as cushy and comfortable as these ones. Fits narrow feet best.
Ugg Kaldwell Shoes
You may not be aware that Ugg has been making comfortable, nonfuzzy footwear for years. Case in point: this midcut boat shoe with seersucker cotton lining, a supple nubuck upper that gives your ankles room to move, and sneakerlike grip underneath. It’s a bit pricier than similar models we tested but also a lot more comfortable.
Clarks Originals Majorca Shoes
The crepe sole and moccasin design of this summer-weight slip-on conjure up our dad’s days as an Eagle Scout troop leader on Lake Winnebago. But the comfortable, therapeutic OrthoLite footbed and soft, bendy suede of the upper, which compresses down to nothing for cramming into a carry-on, is decidedly now.
Keen Timmons Slip-On Shoes
The Timmons has been in our regular rotation for almost a year. Why? It can handle just about any casual endeavor—the boatworthy, nonmarking rubber sole is wedded to a water-resistant leather upper. And its canvas lining and memory-foam footbed have only gotten comfier over time.