Performance plus style equals happy feet.
Patagonia Activist Fleece Waterproof
If your favorite sneaker and hiking boot had a love child, it would be the Activist Fleece ($165). It fits like a tennis shoe on the bottom, but the waterproof suede upper keeps out moisture, just like any good boot. The spun-wool, fold-over collar adds warmth and a touch of flair.
Bogs Classic High Secret Garden
This wellie looks like it would be perfect for summer gardening, but with seven millimeters of waterproof insulation and a moisture-wicking liner, it performs best in a polar vortex. A roomy toe box and supportive arch ensure all-day comfort. $120, bogsfootwear.com
Columbia Minx Shorty Omni-Heat Print
Below freezing? No problem. The Minx ($90) is rated to minus 25 degrees, with 200 grams of insulation and Columbia’s Omni-Heat reflective lining. That means you can roast s’mores to your heart’s content without wanting to stick your feet in the campfire.
Helly Hansen Alstad
Crafted to withstand winter’s worst, this leather boot has a faux-fur lining to keep your piggies warm and a rugged outsole to keep you upright on frozen surfaces. The quilted upper and thoughtfully placed buckle above the ankle make the Alstad ($160) a go-to choice for urban outings.
Keen Bern Baby Bern Lace
There is nothing crotchety about the way this old-school-looking Keen performs. The full-grain leather upper offers both support and warmth—although the mesh lining isn’t super thick, so wear heavier socks. Sage green laces and knit panels on each side add a Southwest vibe. $140, keenfootwear.com
OluKai Haleakala Suede
Haleakala ($225) translates to “scenic national park,” though we really prefer these boots for in-town duty. The wool-blend lining and suede uppers insulate well over skinny jeans, while the full-grain leather upper and rugged outsole protect your feet. Nice: the moisture-wicking footbed is easily removable and washable.