Your relationship with your tailor is crucial: a good one knows your physique and appreciates your worldview. You're trusting him with your appearance in the field of sartorial battle, so to speak, so choose wisely. And once you've got your man (or woman) get the most out of the relationship by adhering to a few general principles.
Know what you’re after.Do you like a break in your trousers? Do you like to show a little extra cuff? These may seem like obvious points, but you’d be surprised how many guys show up for a fitting unprepared to give direction. These are decisions you learn through experience, and you shouldn’t leave them to anybody else, even the most trusted master of the needle and the thread.
Dress accordingly.If you’re having a jacket altered, wear a dress shirt you like—and that fits the way you like a shirt to fit. If you’re having pants hemmed, wear shoes you normally wear: you don’t want to be appraising a pair of tuxedo trousers while wearing your Jack Purcells. (So no, we’re not recommending you wear Converse with a tux.)
Be reasonable.Re-cutting a coat to narrow the shoulders is a serious job—the tailoring equivalent of open-heart surgery. And you shouldn’t leave either to somebody without proper expertise. A good tailor knows what’s a difficult job, admits as much, and will charge accordingly.
Do some research.When choosing somebody for basic alterations, see what other kinds of work they do. Is he used to opening button holes? If he’s surprised by something you request then he’s not the man to be asking. If you need a trusted name, ask somebody from a store you frequent who they like to use.
Cultivate your relationship.A good tailor, like a good mechanic or bartender, is an indispensable part of your life. If you like his work, tell him, and refer friends—he’ll be more willing to indulge your more nuanced requests, and he’ll get your work done sooner.
