Two unemployed musicians, bass player Jerry and saxophone player Joe, witness the St. Valentine's Day Massacre in Chicago. In order to escape gangster Spats Palazzo and his henchmen, they dress as women and join Sweet Sue and Her Society Syncopaters, an all-female band about to leave town for an engagement at a Miami Beach hotel.

Complications arise when Joe, now known as Josephine, falls in love with beautiful band singer Sugar Kane, who has a slight drinking problem that tends to interfere with her ability to choose a romantic partner wisely. More than anything, Sugar wants to marry a millionaire, prompting Joe to disguise himself as the man of her dreams.

Meanwhile, wealthy and elderly Osgood Fielding, Jr. is pursuing Daphne, unaware she really is Jerry in drag. As much as he knows he needs to reveal his true gender to his over-amorous paramour, Jerry is beginning to enjoy all the expensive gifts bestowed upon him on a regular basis.

Total chaos erupts when Spatz and his gang descend upon the hotel and realize who Josephine and Daphne really are