Don't go long.
Credit: Photograph by Chad Springer

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.