How to dress with style when it's freezing out

If only Milan had Montreal’s climate

(Krane; Wings + Horn; Suit Supply)

(Krane; Wings + Horn; Suit Supply)

My morning commute begins in the dark at 6 a.m. It’s very cold, and my winter go-to—a peacoat—isn’t cutting it. What else works well with a suit?

One very warm and sophisticated solution would be a slim-fitting, three-quarter length, cashmere topcoat. However, in cold spells and Winnipeg, this is inadequate and so a parka—one longer than your suit jacket—is in order. It should fit slim and be free of technical accoutrements, like reflective strips, compasses or frayed ski passes. Krane’s Jonas coat, Wings + Horn’s Fishtail Parka and Canada Goose’s Chateau Parka are all stylish, all sturdy and all Canadian made.

This past fall I bought a down-filled vest. I’m fairly certain I can wear it to the office, but can’t decide if it should go over or under my suit jacket.

If your vest fits comfortably beneath a properly tailored suit jacket, go for it. Consider it a three-piece suit with a practical twist. (You would apply the same thinking to a V-neck sweater, right?) If, however, wearing your vest in this manner makes it difficult to button your coat, wear it on the outside. Puffy vests are okay. Puffy men are not.

In the winters of my youth, I remember my father donning thick rubbers every morning. Is this still standard practice?

I can only assume you refer to your father’s galoshes. If you have something else in mind, you might rather speak to my father (he’s a psychiatrist). Protecting leather shoes is a perennial winter quagmire, and your father—like mine—favoured the classic solution, perhaps patronizing Tingley, who invented galoshes a century ago. Swims, a Norwegian line, offers a contemporary, clean-lined alternative in standout colours. But I think your best bet—beyond stashing a clean pair of kicks at the office—is to invest in a pair of sturdy but elegant boots. I own a pair of rubber-soled Grenson pebble leather boots, which look terrific with a heavy wool, tweed or flannel suit, and which, like the British craftsmen who made them, can stand up to all sorts of weather. Alden’s Original Workboots and Wolverine’s 1000 Mile boots are similarly rugged but office-appropriate.

My wife gives me hell for wearing a T-shirt under my dress shirt, but the alternative—freezing outside, schvitzing inside—seems worse. Who’s right?

Your wife, as always. There is no more efficient way to signal to the world a lack of attention to detail than a flash of T-shirt collar beneath your dress shirt. A deep V-neck is a viable alternative, provided your dress shirt is thick enough to conceal any trace of the garment. Then, your undergarments will be effectively invisible, and your wife will need to find a brand new reason to give you hell.