The Monkees (1966)

S01E09 The Chaperone

Davy has developed a crush on Leslie, the daughter of retired General Harley Vandenberg (Arch Johnson). When the actual chaperone, Diana Chesney, shows up intoxicated, Micky steps in to impersonate her at a gathering. His decision to don a female disguise adds a layer of chaos as he tries to help Davy navigate his feelings while keeping the party under control.