The Five Questions Your Tailor Should Ask (And One You Should)
Most guys walk into a tailor expecting to be measured and quoted. That's not how this works.
A proper consultation feels more like therapy than shopping. Your tailor should be asking questions that have nothing to do with your chest size.
"What do you do for work?" Not small talk. A lawyer needs different armhole mobility than a surgeon. Someone presenting to boards needs pockets that don't bulge. Your job dictates construction choices most guys never consider.
"How do you commute?" Drive everywhere? We're thinking about wrinkle resistance and seat wear. Walk a lot? Trouser weight matters. Fly constantly? That changes everything about fabric choice and fit.
"What's your build doing in five years?" Honest question. Twenty-five and hitting the gym? We'll cut with room to grow. Forty-five with a desk job? Different approach entirely. A good suit should work through reasonable body changes.
"Show me a suit you love wearing." Not a picture from Instagram. Something hanging in your wardrobe that you actually reach for. How it fits, why it works, what bugs you about it - that tells us more than any measurement.
"What's the worst thing about your current suits?" Here's where guys get specific. Too hot. Shoulders too wide. Trousers always need hemming. Can't raise my arms. These aren't just complaints - they're blueprints for what we're building.
But here's the question YOU should ask: "What would you do differently if this were for you?"
This cuts through the sales pitch. A good tailor will tell you honestly - maybe suggest a different cloth, adjust the silhouette, skip an upgrade that won't make a difference. They're thinking about what works, not what costs more.
If your tailor just measures and quotes without this conversation, find another tailor. Anyone can follow a pattern. The difference between a suit and YOUR suit happens in these first twenty minutes.
The best bespoke relationships start with questions, not answers.