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There is a morning every October — it lands mid-month, give or take a cold front — when the fall coat stops being an answer. The wind finds the gap between your lapel and your collarbone, and the walk from the garage feels longer than it did on Friday. That morning is when most men start thinking about how to choose an overcoat. It is also, by two or three weeks, too late to be starting. We wrote last month about buying the coat before the first cold snap breaks the size runs. Consider this the companion piece: what to actually look for once you are standing in front of the rack.

The suit decides, not the mirror

An overcoat has one job that outranks all the others: it goes over tailoring. That sounds obvious, and yet the most common overcoat mistake we see walks in every November — a coat bought on a Saturday, tried on over a sweater, that now strangles a suit jacket at the shoulders and shows two inches of blazer below the hem. A coat that cannot close comfortably over your jacket is not your coat, whatever the label says.

So the first rule costs nothing: wear the suit, or at least the jacket, when you shop. The coat's shoulder must clear the jacket's shoulder without a ridge. The sleeve must cover the jacket cuff completely — the coat is the outermost layer, and nothing should show below it but your hand. The hem should clear the jacket's by a generous margin.

Length is where we will offer an opinion. The car coat — the shorter, thigh-length cut — has owned the last decade, and it makes sense for the man who drives to the office door. But if your winter involves actual walking — a métro platform, the long side of a client's parking lot — buy the longer coat and cover your knee. Nobody standing on Peel in a January wind has ever wished his coat were shorter.

How to choose an overcoat cloth: wool outside, Montreal inside

We hold the position that wool reads as clothing and nylon reads as equipment, and we are not softening it for coat season. A wool overcoat over a suit is one of the few combinations in menswear that cannot be improved. The trouble is that a traditional wool coat drinks a Montreal November — those wet weeks before the real cold, when the snow can't decide what it wants to be.

This is why the coats we bought hardest this fall are wool with an answer sewn in. The blue wool Rain System overcoat from Luigi Bianchi Mantova ($2,260) is pure wool on the face — it looks like the coat your most elegant uncle wore — with a weatherproof membrane bonded behind it. Rain beads and rolls off. The same house cuts it in taupe, with a hood hidden in the collar ($2,175). A hood folded into the collar of an Italian overcoat may be the least Italian idea we have ever admired, and the most Montreal: invisible in the Tuesday meeting, deployed in the freezing drizzle outside it.

On colour: dark blue before black. Black is correct over a dinner suit and severe over nearly everything else; a deep blue or a taupe does everything black does and flatters more faces while doing it. If your tailoring leans gray and brown this season — ours does — taupe is the quietly confident pick. And if the car coat really is your answer, because you drive and you said so, the Corneliani technical cashmere we wrote about last month remains the one to beat.

One coat, bought right

You do not need three overcoats. You need one that fits, and the arithmetic is on your side: a coat worn November through April, over everything you own, works more days per winter than any suit in your closet. Price it per wearing and the good coat embarrasses the cheap one by February.

Fit, then, is where the money either works or doesn't. Our tailors can shorten an overcoat sleeve in a week and quiet a body that billows. What they cannot do — we say this about jackets, and it is doubly true of coats — is fix a shoulder. Buy the shoulder. Alter the rest.

And a line of honesty about the week of minus twenty: that week belongs to the parka, and there is no shame in it. The overcoat is for the tailored months on either side — which, in this city, is most of them.

The practical part. It is October, and the size runs are still whole; by mid-November the middle sizes are spoken for, and the man who waited chooses from what is left rather than what is right. The outerwear wall is as deep right now as it will be all year. Come try the coats over the suit you actually wear — or book a fitting and we will handle the sleeves while you decide on the colour. The first real cold is coming either way. You can meet it dressed.