As a rule of thumb, leather shoes will stretch the more they are worn, so make sure they are! VINNY's own rules of thumb are as follows:

YOU CLAIM PATIENCE IS YOUR VIRTUE, BUT LEATHER SHOES AIN'T YOUR (usual) GO-TO
— size down one from your sneaker size

IN CASE YOU HAVE WIDE FEET OR SIMPLY HATE BREAKING IN NEW SHOES
— don’t change your habits

As a rule of thumb, leather shoes will stretch the more they are worn, so make sure they are! However, VINNY's own rules of thumb are as follows:

IF YOU ARE GONNA PUT A SOCK ON IT
— size it up for comfort

IN OTHER CASES
— they might hurt breaking in, but they'll be worth your while