Some men, like MANual contributor Gay Talese, who is descended from Italian tailors and grew up a walking advertisement for his father’s tailoring business, come by their love of the sartorial craft naturally. Others, like myself, earned their appreciation the hard way—good luck finding a nice-fitting off-the-rack suit when you’re 6’5”. Growing up, my experience with tailoring couldn’t have been more different from that of our esteemed correspondent. My first couple of suits came not from my father’s atelier but from the local mall, where the salesman was the style guru. And the tailor? He was the vaguely Gollem-like guy who emerged from somewhere in the back in order to take a few cursory measurements and, in so doing, transform a massively oversized jacket into something that was, frankly, still massively oversized.
Luckily, you grow up, and in the process you learn a few things about how clothes are supposed to fit. You come to appreciate the pleasure of buying a great-fitting blazer or suit, and—with just a few small but essential tweaks—having it magically transformed into something that looks and feels like it was made just for you. This is true whether you’re buying new (from Gilt or elsewhere) or, say, vintage.
So find yourself a crack tailor, and invest in that relationship. And I do mean relationship. A common misconception about the men with the measuring tape is that that they are there simply to take instruction. In fact, a good tailor is more than just a needle for hire. He’s the sartorial equivalent of a professional golfer’s caddy, whose primary job isn’t just to carry clubs, but to measure and to provide counsel: to point his man in the right direction, to help steady his nerves when the time comes to make a big decision and —politely but firmly—to steer him into making the right call. In other words, to know what’s good for him. The older you get, the more you tend to value good advice, whether it’s offered in front of a dogleg right or a three-way mirror.