He need not be an Italian maestro or have apprenticed on Savile Row. You're just getting your pants hemmed, not constructing the definitive suit for a power lunch at 21 with Jay McInerney. Most importantly, this man should recognize you. He should know your sense of style—that you don't like a break in your trousers, that you're partial to silhouettes on the straight and narrow. He'll also happily turn your order around quickly, when needed.
It's a relationship every man should have. It begins by showing due respect to the skills involved. You appreciate what can be accomplished and are realistic in your expectations. He, in turn, understands what you're looking for, and doesn't overpromise or oversell. If you have the good fortune to come into an ancient Savile Row suit you want entirely re-cut (the sartorial equivalent of open-heart surgery), then track down an English tailor who makes his own suits. Otherwise, keep it local, and pay in cash.
A maître d', a mechanic, a fly fishing guide, even a ticket broker—these are the names of men you should have in your arsenal. They connect you to your interests then help you improve them; they're enablers in the best sense. You choose the clothes, but the tailor is the translator—the last set of hands that touches the thread before you wear them. It's best if those hands are trusted.
Every Man Should Have...