According to fashion expert Brock McGoff an adult male only needs six pairs of shoes for almost every day. Start with white canvas sneakers and light brown boat shoes for warm weather casual. A pair of medium brown dessert boots (chukkas) for jeans, cords or chinos. Dark brown loafers for business casual, brown wingtips for business downtown. And a pair of black cap toe oxfords for special occasions from black tie to funeral. If you’re a country guy, add boots for work.