Youthful but sharp enough that you won’t get mistaken for an undergrad. Clockwise from left: Cerruti 1881 Paris Coat, $1,950, The Webster Miami, 305-674-7899; Scarf, $270, Alexander Olch, 212-925-2110; Rugby Shirt, $340, dunhill.com; Glasses, $495, Cutler and Gross, 212-431-4440