Color Does the Heavy Lifting

The color of a shoe decides how many outfits it works with. Brown and burgundy leather are the quiet workhorses: they sit happily with navy, grey, olive, and most denim, so a single brown pair stretches across far more looks than black.

Save black for the most formal end, with dark suits and black tie. If you are buying one dress shoe, make it brown and reach for black only when the occasion truly calls for it.