Merrell Wilderness Canyon Boot
To celebrate the company's 30th birthday, Merrell redesigned the classic Wilderness boot. This version is every bit as tough but, thanks to modern materials, 30 percent lighter and not quite as stiff out of the box. You might see some hipsters rocking the classic black-boot-blue-lace combo; consider it flattery.
TAGS: ICONIC, WATERPROOF
Birkenstock London Shoe
After being jammed in too-tight alpine boots all day, we loved the London's roomy toe box and comfy-as-ever moldable footbed. And kudos for changing it up with heathered wool: even sworn enemies of hippie sandals liked the London's new look.
TAGS: MOLDABLE, LIGHTWEIGHT
Sorel Mad Boot Lace
The water-resistant Mad Boot's flexy soles feel antique in a good way. Just don't expect them to behave like Sorel's gold-standard boot: they're uninsulated and not designed for snowshoeing in the Yukon, but rather for trudging to the bar in the snow.
TAGS: CLASSIC LOOK, FINELY CRAFTED
Western Chief Neoprene Boot
If you live someplace where it gets cold and wet, you should own a pair of impermeable wetsuits-for-the-feet. (Take a New York City subway ride in the fall and you'll see that the ladies have already figured this out.) The slip-on Neoprenes are surprisingly comfy and just low-key enough to wear under a pair of jeans.
TAGS: SUPREMELY DRY, EASY ON AND OFF
Keen Timmons Chukka
Part classic chukka, part skate shoe, the Timmons has a bouncy sneaker bottom with a soft but durable nubuck leather upper. And, unlike most of Keen's shoes, this one doesn't have the massive toe bumper that screams out "Amphibious vehicle!"
TAGS: COMFORT, GOOD GRIP
Clarks Tarnaby Boot
With Clarks's signature natural crepe outsole and a rubber strike pad in the one-inch heel, the Tarnabys are as comfy as they are handsome. Plus, being seven inches high and cut from water-resistant leather, they're all but impervious to the elements.
TAGS: SLOP-PROOF, SHARP LOOK