How the legendary Ivy League tailor dressed everyone from J.F.K. to Andy Warhol—and brought color, wit, and a little anarchy to the button-down look

By Constantine A. Valhouli

What sort of person shopped at Chipp? For G. Bruce Boyer, the former Town & Country editor, the answer was a character like Phineas from John Knowles’s A Separate Peace: “The one who used his school necktie as an impromptu belt and then charmed the headmaster’s wife by saying that he knew it was wrong but it would’ve been worse if his trousers fell down at the Sunday tea. That is the archetypal Chipp customer.”

Like the Andover Shop and other traditional clothiers, Chipp grew out of J. Press. But it was always the bad boy of the family, READ ON