A straightforward, curated guide to help you make informed choices and avoid buyer's remorse.

1. Camper Hardwood ($270): With a Vibram lug sole, sturdy leather, and a Gore-Tex lining, this wingtip boot is just as suit-friendly as it is snow-ready. It’s a classic silhouette — just not a classic snowboot silhouette.
 
2. Timberland Chestnut Ridge ($175): Between a full-grain waterproof leather upper and lug outsole lies a gusseted tongue (to keep out snow, slush, and wintery gunk), vintage-inspired stitching, and Timberland’s proprietary anti-fatigue foot comfort technology. These boots will outlast every storm you encounter this season (and the next), yet they’re streamlined enough for daily wear.
 
3. Timberland Britton Hill Moc Toe ($190): Get maximum weather resistance without sacrificing an ounce of casual, cool handsomeness. With a mesh lining for breathability and Timberland’s exclusive SensorFlex technology (for foot support and flexibility), the Britton Hill Moc Toe promises all-day comfort whether you’re shoveling driveways or sitting in front of a computer.
 
4. Sorel Cheyanne ($135): This is what we picture of when we think of classic winter boots. A duck hunting silhouette in a versatile colorway, the Sorel Cheyanne keeps out water and frigid temps thanks to a seam-sealed construction and Thinsulate lining, holding its own against temps as low as -25° Fahrenheit. Pair it with corduroys for a classic cold-weather look.
 
5. Sorel Caribou ($150): For those days when standard boots won’t cut it, the Sorel Caribou is our go-to. As Sorel’s first boot — made to hold up in Canadian winters, promising warmth in temperatures as low as -40° Fahrenheit — the Caribou put the brand on the map over 50 years ago and has kept it there ever since. Ideal in heavy snow, the Caribou’s seam-sealed, waterproof nubuck leather upper and Sherpa-lined, insulated inner boot bring you eye-catching style without sacrificing an ounce of function.
 
6. Sperry Authentic Originals Lug ($155): Ideal for autumn’s chill and moderate winters (where snowfall is light), this boot brings casual, nautical vibes to slick boat decks and slushy sidewalks alike. With a waterproof leather upper, cozy flannel lining, and lug sole featuring Sperry’s proprietary Wave Siping tread, the Authentic Originals Lug Boot allows you to indulge in classic boat shoe vibes, even when the ship’s in storage and the beach is closed for the season.
 
7. Native Fitzroy ($110): A waterproof sneaker boot made from ballistic nylon and a water-resistant backing, the Fitzroy is heavy on the hiking vibes, but still as airy as everything else in Native’s line. A shock-absorbent EVA outsole boosts comfort and traction, keeping you light on your feet whether in heavy snow or bone-dry city streets.
 
8. Ransom Alpine ($200): A hiking boot with sneaker appeal, the Ransom Alpine is more weather-ready than mountain-ready (but that doesn’t mean you can’t wear it on a hike). Tough, full-grain, water-resistant leather; high-shine hardware; pops of color in the laces, welt, and lining; and a Vibram wedge sole make this one of the most city-friendly, statement boots we’ve seen in a long time.
 
9. Merrell Epiction Polar ($190): A hiking-inspired boot made for city streets and icy adventures, the Epiction Polar promises stability and shock absorption thanks to Merrell’s signature air cushion heel. A jagged sharktooth sole amps up all-surface grippiness, and low-bulk insulation and a mesh lining offer breathability to keep your feet warm (but not sweaty). These aren’t the vaguely orthopedic shoes your grandpa wears, but they’re just as comfortable.
 
10. Sorel Paxson ($150): Tough nylon detailing is contrasted and made more wearable by a nubuck leather upper. Inspired by hard-wearing work boots, with amped up all-weather ruggedness, the Paxson is unmatched among outdoor utility boots (which means it’s guaranteed to hold up against daily, mucky winter weather).