"Many Americans have this idea that if you put on a dress shoe, it has to be black. But Italians—and I myself, especially—very rarely wear black shoes, except for very formal occasions like weddings and funerals. I'm almost always in brown shoes, because they just work with everything. If you're in a pale gray sweater and khakis, you choose a light brown shoe; if you're in a navy blazer and dark gray pants, chocolate brown loafers. The one rule I have is that your shoes should match your accessories. Don't try to wear a deep brown watchband and a black belt and caramel-colored shoes. That won't work. But the beauty of brown shoes is that all the different shades let you communicate something about your personality—you tell the world you have a sense of play and character just by putting something on your feet."
Designer Domenico Vacca on why brown dress shoes do it for him.