A bespoke suit flatters, never shows its age, and has the power to imbue a tinker, soldier, or spy with the sort of confidence he might otherwise find in a bottle. Every man deserves one, but actually acquiring a tailored suit requires more than just taking out the plastic. You have to work with your tailor to build something worthy of a rite of passage. And, yes, that first trip to a serious haberdashery – whether it be on Savile Row, Fifth Avenue, or the streets of Hong Kong's Tsim Sha Tsui neighborhood – is as much of an initiation as any graduation, bar mitzvah, or first kiss.
That doesn't mean that stepping in front of a three-way mirror isn't unnerving. It absolutely is, which is all the more reason to study up before you start playing with fabrics and talking about that Tom Ford sport coat you saw in the pages of 'Men's Journal.' This is no time to rest on your lapels. Before you part with a lot of money on a suit that will be with you for life, you need to have a long conversation with your sartorial spirit guide: your tailor.
Tailors operate on small margins and word of mouth. The field is stunningly – and increasingly – competitive. That means you need to listen, but it also means you need to participate in the process. Here is everything you need to do to help your suit maker create something so long-lasting you'll want to be buried in it.
A tailor will ask you straightaway when you are going to wear your suit. Have an answer ready. Do you wear a suit to work? Do you dress in jeans, and is this going to be your only suit? Are you going to wear it to your wedding? To your sentencing? A tailor wants to build a relationship with you, so help him understand your needs. And don't be afraid to speak freely: Tell him what you do for a living, what your office is like, where you live, what the climate is, what problems you've had with suits in the past. If you generally don't like wearing suits, tell him why.
Credit: Photograph by Chad Springer
Don't feel pressure to act more formal than you are. If it's the first time you've been to a tailor, tell him that, too. He won't think you're a greenhorn; he'll be flattered you came to him. Remember: He's been dealing with men for many years. He's seen all types.
If you want to wear a suit to a special occasion (say, your wedding) then work it into the rotation, you can ask the tailor to put on special buttons for the big day. Then you can rotate them out for the rest of the life of the suit. Keep the buttons, of course, and pass them down to your son.