Sorel Chipahko Felt Boots
BEST FOR: DRY URBAN ENVIRONS
We wore this water-resistant wool-and-leather boot nonstop around town, especially in shoulder seasons, because it was warm and cozy and offered just enough traction on leftover ice. Unfortunately, there鈥檚 no easy way to get it on or off鈥攖he buckles are just for show.
Keen Akita High Boots

BEST FOR: SKI-TOWN DINNER OUTINGS
The 2.5-inch wedge on the lets you dress things up without compromising grip. The cork-blended sole held onto ice-covered sidewalks, and the water-resistant leather and microfiber lining did their jobs at slush time. Beware: even with a full-length zipper, fit is limited to slim calves and the skinniest jeans.
Timberland Radler Insulated Boots

BEST FOR: WINTER CAMPING
With double the insulation of the Hi-Tec, a water-resistant nylon shell, and a grippy rubber sole with aggressive tread, the was a staple on winter camping trips. Plus, a pair easily scrunches down by zipping together鈥攖he whole package is about the size of a Nalgene bottle.
Helly Hansen W Maja Boots

BEST FOR: SHOULDER SEASONS
The moccasin-like handled cold temperatures beautifully, thanks to a shaggy micro-fiber-and-faux-shearling lining. The waterproof leather batted away light precipitation, but we wouldn鈥檛 take it in ankle-deep snow or on ice: the opening under the snaps isn鈥檛 sealed, and the ribbed tread doesn鈥檛 have much bite. Runs a half size small.
Ugg Sabene Boots

BEST FOR: SLUSH
Don鈥檛 expect it to keep you warm (it isn鈥檛 insulated), but it will keep you dry. Pull the rubber wellie on come spring, when the sun is thawing the sidewalks into a mess of puddles and slush. The ribbed sole provides some traction, though not on slick ice.
Hi-Tec Sierra Pamir 200 WP Boots

BEST FOR: BLIZZARDS
This is the most foul-weather-ready shoe here, great for hiking in nasty conditions or snow-shoeing. The Vibram sole鈥檚 tirelike tread gripped icy sidewalks, and the light insulation kept our calf nice and toasty. Bummers: the faux fur has an odd bluish tint, and the heel cup runs narrow.