How to Build a Work Wardrobe: What $2,000, $5,000, and $10,000 Buy in Montreal

The question usually arrives quietly, near the end of a fitting: "If you were me, where would you start?" A man has a new position, or a new city, or has simply looked into his closet one September morning and seen nothing that matches the life he now has. He isn't asking about one purchase. He's asking how to build a work wardrobe — the whole architecture of it. After enough of these conversations in our Montreal fitting room, we can tell you the budget matters less than the order. So here is the order, honestly, at three budgets: $2,000, $5,000, and $10,000.

The $2,000 wardrobe: one suit, bought properly

The temptation at $2,000 is to spread it thin. Two suits at six hundred dollars each, a stack of promotional shirts, something left over for shoes. We would rather you didn't. Two mediocre suits read as two mediocre suits, on Monday and on Thursday alike. One good suit, altered to your shoulders, reads as a man who knows exactly what he's doing — and nobody, truly nobody, notices that it's the same charcoal twice in one week.

Charcoal, by the way, not navy. We've argued this before and we'll keep arguing it: charcoal disappears into every room from a morning interview to an evening funeral, and it flatters more complexions under fluorescent light. Jack Victor's charcoal semi-solid Dean, cut a few kilometres from our store, is $1,148 and the best first suit we sell. Add two shirts — white before anything else, then light blue. ETON's white textured twill is $295; the Stenströms equivalent is $325. That's roughly $1,750, and the remainder belongs to alterations, a horsehair brush, and proper dress shirts and hosiery rather than a second, lesser suit. Marcoliani socks cost little and are noticed more than you'd think.

How to build a work wardrobe past the first suit

At $5,000 the wardrobe stops being an outfit and becomes a system. The second suit should differ from the first in cloth and construction, not merely in colour — otherwise you own the same suit twice. Our pick this fall is the blue wool-cashmere Irving from Jack Victor, $1,248: unconstructed, soft through the shoulder, made in Montreal, and just as convincing with the trousers swapped out on a Friday.

Then the pieces for the days a suit would be too much, which in most Montreal offices is now most days. A pair of real flannel trousers — Berwich cuts theirs from Vitale Barberis Canonico cloth, $490 — and a fine-gauge wool crew neck like Gran Sasso's vintage-washed model at $325 will carry you through October to April with either jacket. Shoes: one pair of brown derbies before a second pair of black anything. Magnanni's tumbled-leather Melich V is $750; their taupe suede Garner is $575 and sneaks under a surprising number of dress codes. Add a third shirt and you've spent about $4,900. If the arithmetic ever forces a choice between a third suit and your first serious shoes, buy the shoes. People look down more often than they look up.

At $10,000, stop adding and start upgrading

Here is something a retailer probably shouldn't say: don't spend $10,000 in an afternoon. Spread it across a year, and spend it on depth rather than breadth. This is the tier where made-to-measure earns its keep — if off-the-rack has always compromised somewhere on your frame, a suit cut to your posture solves it permanently, and our tailored clothing wall is where that conversation starts. It's the tier for a textured sport jacket from Corneliani or Luigi Bianchi Mantova, because a man who owns two suits needs a jacket that is emphatically not a suit jacket. It's the tier for a proper fall coat bought before the first cold snap rather than during it, a second pair of shoes — a Santoni cap-toe for the suit days — and a shirt rotation deep enough that nothing gets laundered to death.

What it is not the tier for: a third navy suit. We will talk you out of that one at the counter, cheerfully, even though we stock it.

Where to start on Monday

The sequence, then: one excellent charcoal suit and two shirts. Then a second suit in a different cloth, flannels, a knit, and brown shoes. Then upgrades — made-to-measure, the sport jacket, the coat — as the years and the promotions arrive. Bring us the budget you actually have, not the one you think a menswear store wants to hear, and we'll build the plan to it. Book a fitting, bring the suit you already own, and we'll tell you honestly which list it belongs on.