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Of all the questions men ask us in the fitting room, few arrive as carefully as this one. A client will stand there while we chalk a trouser hem, lower his voice a little, and ask whether he can wear jeans at the office. He usually knows the answer already — half his floor is in denim by Thursday, and nobody has been sent home yet. What he is really asking is how to wear them without looking like he stopped trying. That is a better question, and in a Montreal office that went tie-optional years ago, it deserves a better answer than it depends.

So: yes, you can. With conditions. The conditions are everything.

The rules for jeans at the office

The first rule is wash. Dark and uniform — a deep indigo, a blue-black, a charcoal so even it reads as plain cloth from across a boardroom. Denim earns its place at work by behaving like cloth, not like a souvenir of your weekend, and the lighter and more faded the wash, the more weekend it drags in with it. No distressing, ever. No rips, no whiskering, no sanded thighs. Distressing is leisure's costume, and however relaxed your office has become, it is not leisure.

The second rule is fit, and it is the same rule we apply to every trouser on our racks: jeans are welcome anywhere five-pocket trousers are welcome, provided they fit the way tailored trousers fit. Clean through the seat and thigh. Slim without strangling. And no denim stacking on your shoe — those three inches of bunched fabric at the ankle undo everything the dark wash just earned.

We stock two answers to this, and they solve different problems. Tramarossa cuts its denim in Vicenza and finishes it like tailoring; the blue-black Leonardo in super-stretch denim ($495) is the closest thing we sell to a dress trouser that happens to be denim. PAIGE's Lennox in vintage navy ($335) is the softer American answer — their Transcend stretch recovers its shape through a long desk day instead of bagging at the knee by lunch. If your jeans will live under a sport jacket, take the Tramarossa. If they will live under knitwear, the PAIGE. The rest of our denim wall runs the same gamut, and we will tell you plainly which side of it a given pair belongs on.

What you wear above them decides the verdict

Jeans almost never fail on their own. They are failed by what is above them. The worst offender remains the orphaned suit jacket — half of an old worsted suit pressed into service over denim, too smooth and too structured to agree with the cloth below it, flattering neither. Over dark denim you want texture: a knitted sport jacket, a hopsack, a fine merino crew, a proper collar worn open. A brown knit over blue-black denim is, this season, about the most quietly current thing a man can wear to a tie-optional office.

Then let the shoes do the heavy lifting. A suede derby. A dark loafer. A polished boot once November gets serious. Dark denim with a pressed shirt and proper shoes will outdress half the suits on René-Lévesque; dark denim over a retired running shoe will not outdress anyone, and the running shoe is usually what sinks the whole experiment.

When jeans stay home

A first meeting with someone who has never seen you before. A floor where the senior men still wear suits. Any day you expect to be evaluated rather than merely present. On those days the question is not whether you could get away with denim — you probably could — but whether you want the room spending any thought on your trousers at all. Gray flannel exists for exactly those days, and it asks nothing of your nerve.

Bring them to the tailor — yes, really

Here is the habit that separates the men who wear denim well from the men who merely wear it: they treat jeans as clothing, not as an exemption. The same client who has his suit sleeves shortened to the quarter-inch will wear jeans exactly as they came off the shelf, puddled hem and all. Bring them in. We hem denim every week at the shop on Decarie Boulevard — to the shoe, slight break or none — and we will taper a leg when the seat fits but the line flaps. Bring the shoes you plan to wear them with; it takes ten minutes more and gets the hem right the first time. You can book a fitting here.

The office changed. The standard did not. Dark, fitted, finished — that is how denim passes, in this city and most others.