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Every September the same conversation returns to our fitting room. A client is flying out of Trudeau on Monday — two days in Toronto, then on to New York — and he wants to know how a week of meetings fits into one carry-on. After years of dressing Montreal's travelling executives, we have a firm answer: a business travel wardrobe is not a smaller version of your closet. It is a different discipline, built around cloth that forgives and pieces that repeat without anyone noticing.

The good news is that the discipline is simple. Five days of meetings needs one jacket, two trousers, three shirts, one knit, one pair of shoes. The skill is in choosing which ones.

One jacket, and it had better be jersey

The mistake we see most often is a man packing his best structured jacket. Canvas and shoulder padding are wonderful things — we have argued for them at length in this journal — but they do not fold. They arrive creased at the sleevehead and sulk for the rest of the trip.

A travel jacket should be knitted, not woven. This fall that means the gray mélange wool jersey sport jacket from L.B.M. 1911 — unconstructed, no lining to bunch, cut from a wool jersey that comes out of a suitcase looking the way it went in. Roll it, don't fold it, and it will take a seat in the overhead bin without complaint. At $950 it is the hardest-working garment in this entire packing list.

And we'll take gray mélange over navy for travel, an opinion we hold firmly. A mid-gray jacket sits over navy trousers, over denim on the Friday flight home, over every shirt you own — and the mélange texture hides a week of wear the way a flat navy worsted never will.

Building the rest of the business travel wardrobe

Trousers do the heaviest lifting, so they should be technical. Alberto's Ceramica navy five-pocket is what we send travellers out with: a breathable, heat-reflective fabric that refuses to wrinkle and refuses to bag at the knee, in a five-pocket cut that reads as a dress pant in a boardroom and a casual pant at dinner. Wear one pair on the plane, pack a second in gray, and you are covered from Monday's presentation to Thursday's steakhouse.

Shirts are where most suitcases go wrong. Cotton poplin creases if you look at it sternly. ETON's Signature Twill is the exception — the wrinkle-free finish actually is wrinkle-free, not merely wrinkle-reluctant — and a white and a light blue, folded flat, will carry three days each with no hotel iron involved. Our dress shirt wall holds both, along with the flannels and corduroys that dress a travel wardrobe down for the weekend leg.

Add one fine knit — a navy wool and cashmere half-zip from Gran Sasso, say — and you have the flight uniform, the hotel-bar layer, and the Sunday-morning walk covered by a single garment.

The rules we hold to at thirty thousand feet

Wear the heaviest pieces on the plane: the jacket on your shoulders, the leather shoes on your feet. One pair of shoes only — dark brown, rubber-soled, a Magnanni loafer or derby that survives a rained-on Manhattan sidewalk and still belongs under a jacket. Two pairs of Marcoliani socks more than you think you need, because socks are the one thing you cannot re-wear.

Hang everything the minute you check in. Ten minutes of hotel-bathroom steam while you shower will settle whatever the suitcase inflicted. And never, ever check your tailoring. Airlines lose bags; a man who lands in Toronto at nine for a ten o'clock meeting keeps his jacket where he can see it.

One more opinion, offered freely: the week before a trip is the wrong time to discover your trousers need a hem or your jacket sleeves run long. Our tailors work in-house on Decarie, but good work takes a few days. If autumn has you flying, book a fitting two weeks out, or call us at 1-877-393-2789. We will have you packed, pressed, and boarding with one carry-on — and nothing to apologize for when the jacket comes off the hook in the boardroom.