Clarks Desert Trek Shoes
We鈥檝e tested dozens of modern interpretations of the classic over the years, and we鈥檙e still partial to the original. The crepe rubber sole gives it some heft (it鈥檚 the heaviest shoe here) but also makes it extremely comfy and durable.
Birki’s Classic Skipper Shoe

There鈥檚 nothing better than sliding out of a cycling cleat鈥攐r water bootie, or ski boot, or climbing shoe鈥攁nd into the cloglike Skipper. Unlike the classic Birkenstock (Birki鈥檚 is a sister brand), the , with its five-layer foam-and-cork footbed, takes no time to break in.
Cole Haan LunarGrand Wingtip Shoe

Bright color combinations and enhanced stitching bring the style. A high-tech midsole鈥攖he same stuff Nike uses for its top-of-the-line running shoes鈥攂rings the spring. The result is the best-looking, lightest-weight we鈥檝e ever worn.
El Naturalista Campos El N659 Shoe

El Naturalista achieves comfort the old-fashioned way: like everything the Spanish company makes, the is constructed almost entirely from natural materials (hand-stitched jute midsole and veggie-tanned leather outer). Perforations in the upper help it breathe on hot days.
Sanuk Baseline

Call the Sanuk 2.0. Whereas the original was so flexy you could literally roll
it up, the Baseline has a vulcanized midsole for more structure. The result isn鈥檛 as packable, but it鈥檚 just as cushy, way more durable, slimmer, and (slightly) less casual looking.
Rockport Clearview 2 Chukka Shoe

Like the LunarGrand, Rockport鈥檚 is business up top and performance down low. The ultralight, shock-absorbing footbed is courtesy of Adidas. It鈥檚 a winning mashup, and the Clearview 2 is ideal for any walking-intensive warm-weather trip.