Converse shoes are a staple in many people’s wardrobes. From white to black, to green and pink, and from high-tops to slides, a good pair of “Chucks” can up the cool factor of just about any outfit.

Perhaps the most “of the moment” way to sport classic Converses is with a suit, à la Madam vice president. These low-cut lace-ups easily tone down the seriousness of a tailored suit, but play with ...