During 1929 in Chicago, Joe (Tony Curtis) is a Jazz saxophone player and as well as a ladies man. His partner Jerry (Jack Lemmon) is a jazz double bass player both working in a speakeasy in disguise. Charlie is ambushed afterwards by Spats and he is killed. Joe and Jerry flee and then join sweet sue with her group disguising themselves as women.
They become Josephine and Daphne and as they board a train for their next performance, they spot Sugar Kane (Marilyn Monroe), who is the band’s main vocalist and Ukelele player. Josephine and Daphne become allured and they both want Sugar. They begin fighting among themselves to win her over. In all they have to do, they must remember to keep themselves as women. Joe particularly goes an extra mile to win over sugar after learning that sugar is no longer interested in saxophone players ever since she got broken hearted by them in the past. This makes Joe to work harder for sugar. Joe goes ahead to pretend that he is a wealthy man in Miami