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We have watched a man deliberate between two nearly identical navy jackets for the better part of an hour, then pick his trousers in the time it took us to fold the first one. It happens every week, and it has the priorities exactly backwards. Think about how a working day actually goes: the jacket is over the chair by half past nine, and what the room sees from then on is shirt and trouser. Knowing how to choose dress pants is the least glamorous skill in menswear and one of the most valuable — and with the first cool mornings settling over Decarie Boulevard, this is the week to acquire it.

Begin with the rise, not the waist size

The rise — the distance from waistband to crotch seam — determines more about how a trouser looks than any other measurement, and it is the one measurement nobody checks. Twenty years of low-rise fashion trained men to wear trousers on their hips, where the waistband digs in the moment you sit, the shirt works loose, and the leg collapses over the shoe. A proper dress trouser sits at or near the natural waist, so the cloth falls in one clean line from waistband to hem. It feels old-fashioned for about a day. Then you sit through a two-hour meeting in comfort, and the argument is over.

The second rule: buy for the seat and thigh, never the waist. Our workroom can take in a waistband or taper a leg in an afternoon; nobody can add cloth that is not there. If the seat pulls when you stand, the trouser has failed, whatever the label says. In our experience most men wear their trousers one size too slim and one break too long, and correcting both costs nothing more than a proper fitting.

This is flannel country

A smooth worsted trouser is correct twelve months a year. But a Montreal calendar hands you seven months in which there is a better answer. Flannel is wool brushed to a soft nap: it holds warmth without weight, drapes instead of clinging, and stays matte where worsted shines. Under a sport jacket, or with nothing more than a fine knit, it looks like the season itself.

The pair we would start with is Berwich's Morello in navy mélange flannel — cut in Italy with a single pleat and a sensible rise, the kind of trouser that makes everything worn above it look more considered. A step further up, Marco Pescarolo's wool-and-cashmere flannels are, plainly, the finest trousers in the store; clients who try the brown flannel five-pocket tend to stop looking after that. Both are on the racks now, alongside the rest of our dress pants for fall.

On colour, our advice has not changed in decades: mid-grey and navy first. A grey flannel trouser goes with every jacket you own, which is precisely why it never looks like you tried too hard.

How to choose dress pants when your office gave up suits

Half our clients now dress for offices that sit somewhere between tailored and casual, and the honest solution is the five-pocket trouser: the architecture of jeans, executed in dress cloth. Marco Pescarolo's Nerano five-pockets in navy wool-stretch will pass any client dinner in the city with a knit and loafers, and still look right at a Saturday lunch. Alberto's Ceramica five-pocket does the same job in a technical fabric that shrugs off a commute or a week of travel without creasing. We keep these with the casual trousers, but make no mistake — they are doing dress-trouser work.

The hem is the handshake

However good the cloth, a trouser is won or lost in the last ten centimetres. Our position: a single, slight break at most, and none at all if you favour loafers. A pool of surplus fabric at the ankle undoes everything the drape accomplished above it. Cuffs belong on pleated flannels — they add weight exactly where flannel wants it — and stay off plain-front trousers.

Every pair we sell is hemmed in our own workroom, and we would rather you bring the actual shoes you plan to wear than guess. If your current trousers have never met a tailor, bring those too; more of them are rescuable than you would think. Book a fitting, and we will sort the rise, the break, and everything in between.