The streets are starting to look messy, but that doesn’t mean you should, too. For pure utility, nothing beats a pair of Sorel-style boots, but when your evening includes cocktails and not just dog sledding, you don’t want to sacrifice style for warmth. Luckily, you don’t have to.
Winter Chucks: Chuck Taylor All Star Bosey
Chuck’s old-school style gets winterized: The difference between your favourite kicks and these John Varvatos high tops is a shearling lining and hearty, waterproof leather. US $200
Blue Collar Classics: Red Wing 2206
This 105-year-old Minnesota shoemaker has tweaked its classic work boot slightly to prep it for a winter outdoors; its Thinsulate liner will keep your toes toasty on the frostiest days. US $200
Boat Shoes: Frye Nolan Lace-Up
Though the lake’s frozen, you need not abandon your easy-going nautical style. Chunky laces and hand-antiqued leather reference the classic boat shoe; the sturdy rubber sole and high boot cut are all business. US $178
Vintage Snow Stompers: Doc Martin 1960 For Life 8 Eye Boot
Doc Martins don’t go in style, or out of style; they just last (for a lifetime, guaranteed). Durable leather and sturdy welting mean these boots can handle the worst of winter. US $150
Sleek Feet: Tretorn Klippor
Tretorn will protect your feet against the impending crush of slush. An inventive combination of rubber and leather, with a fleece lining, will keep you dry on treacherous sidewalk expeditions. $120
When possible, manufacturers’ websites are listed. That’s why the prices are in U.S. dollars. For the best price, try a Canadian retailer.
Lead image courtesy of erwan.