The name is a family one. Ralph Ostrove, who had worked at his father Harry's Broadstreet's clothing stores from 1915, struck out on his own in 1938 and named the new venture after his son, Paul Stuart Ostrove. The flagship opened that March 7 at 45th Street and Madison Avenue, where it still stands; its logo is a drawing of Dink Stover, the fictional Yale undergraduate. The legendary merchant Clifford Grodd ran the house from 1958 until his death in 2010, and in 2007 it launched the slimmer, younger Phineas Cole range.
Mitsui owned the brand from 2012 to 2025, building a strong following in Japan, before it was sold in 2025 to Boston private-equity firm Middle West Partners, with former Bonobos chief John Hutchison named CEO.