The man asking was not twenty-five. He was in his fifties, back in a part of life he thought he had closed the book on, and he stood at our counter on Decarie with the particular unease of a man whose last first date predated the smartphone. What to wear on a first date is a question we hear more often than you might guess, from men of every age, and it is almost never asked directly. It usually arrives disguised as "I need something for Thursday night."
We can help with Thursday. Nearly everything else we write about in these pages — boardrooms, interviews, galas — is about dressing for authority. A first date is the one evening that runs in reverse. You are not trying to win the room. You are trying to be easy to sit across from.
What to wear on a first date: the two mistakes
They are opposites, and they are both nerves showing. The first is armour: the full worsted suit, reached for because that is what a man reaches for when the stakes feel high. Across a small table in a Plateau wine bar, a suit does not read as effort. It reads as a job interview, and it leaves her wondering which of you is being evaluated. The second is the borrowed costume — the man who dresses twenty years younger than his driver's licence because he suspects the evening demands it. It never does. We made a version of this argument in October about dressing after fifty; it is doubly true across a table for two.
The aim is simpler than either: look like yourself on a very good day. Clothes chosen with care and worn without ceremony — and nothing, nothing, making its first appearance that night. We hold to that rule for interviews. It holds here for the same reason: a new garment is one more thing in the room asking for your attention.
The flannel shirt does the work
If we could hand every man one garment for this assignment, it would be a dark, quietly patterned flannel shirt. Flannel solves the date's central problem, which is how to show effort without showing armour. It has the collar and cuffs of a dress shirt, so it reads as intention. It has the soft, brushed surface of a sweater, so it reads as warmth. A crisp white poplin at dinner says you came straight from the office. Flannel says you went home, thought about it, and changed.
The one we keep reaching for this month is Stenströms' dark gray check flannel shirt — twofold cotton brushed to a soft hand, a gray-and-beige check that gives the eye something without asking for attention, mother-of-pearl buttons, and the Swedish shirtmaker's moderate cut-away collar, which is the real argument: it stands open properly, with structure, no tie ever intended. $380, and it machine washes at home. Under a soft jacket if the restaurant is the kind whose name you repeat twice on the phone; on its own if it is a bar. Below it, dark denim under the usual rules — dark, uniform, nothing distressed — or a gray flannel trouser if the reservation deserves it.
One living colour, and the shoe with no story
If the plan is drinks rather than dinner — and in a Montreal November, most first meetings are a seven o'clock drink — a fine-gauge knit can carry the whole evening. Here we will argue for something we rarely argue for: colour. Not brightness. Life. Gran Sasso's aqua blue half-zip is virgin wool with a tenth of cashmere, knitted superfine in Italy, in a soft aqua mélange with gray contrast and brown piping tucked just inside the collar — a detail that only shows at close range, which is exactly the range a date is conducted at. In a month when every other man in the bar has retreated into navy and black, one quiet, unexpected colour does a disproportionate share of the talking. $415, and the zip earns its keep on the cold walk between the bar and wherever the evening goes next.
Shoes: dark, clean leather, with no story to tell. This is not the night for the black oxford that announces dinner is business, and it is emphatically not the night for the running shoes that announce you came from the gym. Magnanni's gray Cote Lo threads the needle — a hand-painted calfskin sneaker from the same Spanish house that makes our dress shoes, with elastic lacing that slips off without a struggle, which matters in a city where a good evening sometimes ends at an apartment where the shoes come off at the door. $595, and Magnanni runs generous: take a half size down. Whatever ends up on your feet, it should be broken in and looked after.
The last thing on your mind
A word about the week before. If the shirt wants a sleeve adjusted or the denim needs a proper hem, our tailors can still turn that around in days — a sentence that stops being true in December. Book a half hour, and come in with the reservation already made; telling us where you are going is half the work of dressing for it.
Then stop thinking about it. That is the entire point of getting the clothes right beforehand: at the table, they ask nothing of you. We can press the shirt, set the hem, and send you out the door looking like yourself on a very good day. The conversation, happily, is yours.
