Unless you're attending a funeral, break up a basic gray-and-navy combination with a sober pattern. On Dao-Yi Chow, 37, fashion designer for Public School NYC: Two-button wool-and-mohair jacket ($1,320), cotton shirt ($385), and wool trousers ($595) by Prada; silk tie ($185) by Ralph Lauren Purple Label; steel Colt automatic watch ($2,545) by Breitling; silk pocket square ($90) by Brioni. - Esquire.com