Used to be, the rules for color matching were pretty easy -- black shoes with black, brown shoes with brown, and then a few murky creative areas involving blues, grays and cordovans. These days, the rule is that there are no rules. Whether you're a rules guy or a break-the-rules rebel, khaki can be an intermediary between black and brown.
Old School
The GQ website warns against wearing blacks with browns. "Black and black is a rule. Of course, rules are made to be broken, but it takes an uncanny sense of style to get away with breaking them," Style Guy Glenn O'Brien wrote. Black is also "not very flexible," writes Antonio Centeno, founder of the Real Men Real Style website. As for the shoes, black is dressier and brown can seem more casual -- a point in their favor if you're pairing them with a polo shirt and khakis of whatever color.
New Rules
Plenty of celebrities seem to be going for the black shirt and brown shoes combo with their khakis. If it's your style -- and if you like to be noticed -- why not go boldly wherever you're going. If it doesn't go over well, you can wear different shoes next time.