Just like that guy in Austin Powers who couldn’t stop the steamroller, you can’t prevent winter from smushing you with its inclemency. The best you can do: boots. Really warm winter boots. We prefer these:
Brand new from Oak Street Bootmakers, the Color 8 Trench Boot is the perfect union between practicality and style. Rich, deep brown chromexcel uppers; tough dainite outsoles for grip during messy back-door cold fronts. Good to pair with a suit. Also worth a peek: their superb collaboration with traditional English gunmakers Westley Richards.
You’ll also wanna grab a few pairs of new trail socks for comfort and insulation. Not to mention they look damn handsome, too.
The biggest sneaker of all time gets the waterproof update. For keeping it casual in mixed rain and snow, you’ll want these Chuck Taylor All Star Rubbers. Fresh monochromatic colorways. Cozy French terry lining. Gusseted tongue to keep moisture out. Call it a blessing in disguise.
For trekking the Chicago tundra, we’re fans of Native’s Fitzsimmons boot. They’re inspired by mountaineering boots of yore. Lightweight. 100% machine washable. And so reasonably priced you won’t think twice about crushing murky curbside moats. Think of ‘em as snow tires for your feet. Very stylish snow tires.