Pants Fit — Pants should hang cleanly off your waist and hit right on or slightly below your shoe. If they are bunching up at the bottom, they are too long, and you are dressing like a dirty insurance salesmen.

Ask your tailor (your future best friend) for a little break. Every man looks good in pants with a little break. This means your pants hang over your shoe a 'lil bit. More rakish dudes can ask for no break, which hits right at the shoe. It's more fashionable and edgy, but it makes your legs look shorter and is not recommended for more robust frames.

Critical and related: Suit pants ain't jeans. No one wants to see your coconuts or calves through brushed wool. Give everyone some room.

Photo: Courtesy of Elliot Aronow