Some Like It Hot is perhaps the best known Hollywood film to feature cross-dressing as part of the plot. The two male leads, Jack Lemmon (Jerry) and Tony Curtis (Joe), spend much of the film dressed as women, and their dress animates the narrative first by allowing them to become close to Marilyn Monroe's character, Sugar Kane, while preventing them from pursuing her. At the same time, Jerry's impersonation brings him to the point of marrying a millionaire, Sugar Kane's stated ambition.
The film won the Academy Award for Best Costume Design, the third such award for the Australian designer, Orry-Kelly. Although the most iconic costume was Marilyn Monroe's black beaded cocktail dress (images attached in link below), a great deal of trouble was taken over the costumes of Lemmon and Curtis. Both actors felt that, however absurd and comic the premise, they needed to be convincing as women and demanded that Orry-Kelly design their dresses as well as Monroe's. The result is so thoroughly convincing that Jerry comes to think of himself as a woman when he considers marriage to Osgood "for security."
By the end of the film, Jerry's dress has propelled him into a peculiar situation from which he cannot escape even by tearing off his wig and revealing his masculinity. Meanwhile, Joe has stopped pretending to be a woman, even as he describes himself to Sugar Kane as "a liar and a phony." The convincing costumes have ironic consequences for both men, as Joe's narrative ends in romance and Jerry's in farce.