After dressing down the fifties with Some Like It Hot, director Wilder comes out swingin' for the liberated sixties. Bud Baxter (Jack Lemmon) is a low-level lackey at an insurance company who trades his bachelor pad for promotional benefits. A parade of philandering managers passes through his pad, complicated further when the head of HR (Fred MacMurray) begins ogling one of the apartment building's elevator operators (Shirley MacLaine). There's nothing funnier than the gray flannel suit set in the throes of libidinous buffoonery. But hapless Bud realizes that for the possibility of happiness, he must shed his tightly tailored suit and get a life, not life insurance.