Brown shoes

Brown is... pedestrian. It's provincial. It's the color of compromise, the color of settling. Appropriate only if you're a divorce lawyer in Westchester or a financial advisor who thinks wearing a quilted vest counts as business casual.

Black. Always black. Preferably cap-toe Oxfords—John Lobb, perhaps, or the Edward Green Chelsea if you must venture slightly off the reservation. Sleek, understated, classic. Black is controlled. Dominant. It communicates power without needing to scream.