Sidney Winston founded Chipp in 1945 following many years with J. Press. Chipp gained a reputation for catering to clients with discerning tastes. The company was responsible for popularizing the preppy clothing canon with innovations like patch madras pants, embroidered corduroys, and novelty ties. Chipp had a longstanding relationship with American President John F. Kennedy, providing custom-made suits, shirts, ties, and other items for the former president.