Winter months pose a certain challenge. You’re out there battling the snow, the rain, the mud. It’s cold and messy and you need the right gear. The easiest thing to do is forget your sense of style and just throw on the warmest gear you can find. But it’s not the answer. There’s a better way. The first thing to do is get the essentials right: proper footwear to keep you warm and dry without skimping on looks. Then let the rest follow — great outerwear, a strong knit, the right trousers and of course, good accessories.
Best for Anything
Sorel’s waterproof chukka is the dream come true. At first glance, it’s a good looking leather lace-up. In reality, it is so much more. It’s waterproof and equipped with a rugged rubber sole for added traction should the weather turn against you. You can truly wear it any time whether you need the added protection or not so you’ll always be fully prepared. Styling is easy with this one. We paired it with a quilted olive jacket, earth-toned pullover and slim medium-wash jeans.
Best for Rain
Rain can be a real bummer. However, there is nothing disappointing about these rain-ready chelsea boots. They’re easy to slip on, they’ve got a sleek profile and they’ll keep your feet 100% dry. Pair them with dark wash denim, a Gore-Tex jacket and woolen sweater and your commute will be (relatively) painless.
Best for Snow
For the snowiest of days, there is no skimping on a good boot. It really doesn’t get better than the Caribou Boot from Sorel. It has a removable and washable felt inner lining, sherpa snow collar and a vulcanized rubber shell with AeroTrac outsole for extra toughness. Pairing it with a top-notch puffer, slim chino and patterned, hefty knit and you’ll be more than just merely prepared — you’ll look good doing it.
Sorel: Caribou Boot $160
Woolrich John Rich & Bros.: Sierra Supreme Short Jacket $650
Norse Projects: Arlid Rough Fairisle Sweater $250
Naked & Famous: Slim Chino – Navy Stretch Twill Pants $155
Howlin’: King Jimmy Hat $68