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’s no easy way to get it on or off—the buckles are just for show.
Keen Akita High Boots
BEST FOR: SKI-TOWN DINNER OUTINGS
The 2.5-inch wedge on the Akita High 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 Radler was a staple on winter camping trips. Plus, a pair easily scrunches down by zipping together—the whole package is about the size of a Nalgene bottle.
Helly Hansen W Maja Boots
BEST FOR: SHOULDER SEASONS
The moccasin-like Maja handled cold temperatures beautifully, thanks to a shaggy micro-fiber-and-faux-shearling lining. The waterproof leather batted away light precipitation, but we wouldn’t take it in ankle-deep snow or on ice: the opening under the snaps isn’t sealed, and the ribbed tread doesn’t have much bite. Runs a half size small.
Ugg Sabene Boots
BEST FOR: SLUSH
Don’t expect it to keep you warm (it isn’t insulated), but it will keep you dry. Pull the rubber Sabene 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 waterproof duck-boot-sneaker mashup is the most foul-weather-ready shoe here, great for hiking in nasty conditions or snow-shoeing. The Vibram sole’s 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.