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.
Don't go long.
The biggest tailoring mistake most men make is wearing their pants too long. Trousers should never be pooled around your brogues as if you've raided your taller brother's closet. That's not to say they should be as short as Thom Browne's either. Emulate the Italians, who often wear their trousers just to the tops of their shoes. If you're not showing any sock, all the better. Feel free to add a little break in them if you feel strongly about it.
This is a subject where you might have to be a bit assertive with your tailor. If you prefer your pants with a clean look and no break, you'll have to insist on it. Most tailors' default position is to go long because they often have older clients who prefer a more generous cut to their trousers.
Credit: Photograph by Chad Springer