Chaplin had twice previously donned female attire at Keystone, in A Busy Day (1914) and The Masquerader (1914). A WOMAN was Chaplin's last and finest female impersonation, a then-popular device among comedians (Julian Eltinge built a career and fortune on it).

The first half of the film is a typical park comedy (filmed at present-day Lincoln Park, a few miles northeast of downtown Los Angeles), in which the Tramp causes havoc as a result of his mischief with a flirtatious woman, soda bottles, and a nearby lake. The second half requires Charlie to disguise himself as a lady in order to be near Edna, his newfound sweetheart, after her father has forbidden her to see him.