Walking a Mile in Someone Else's Heels
From the beginning it is immediately apparent that Joe and Jerry (especially Joe) are very interested in meeting and two-timing women; their main interest is sex, but they do not consider the particular perspective of the fairer sex. When the two musicians have to don women's clothes to escape the wrath of Spats Columbo, they realize the subtle inconveniences of being a woman. Rather unexpectedly, they immediately take to their roles, realizing just how unwanted so much male attention is to women. In this way, the gender-bending serves as not only a sight gag, but also a thematically significant element of the plot; in adopting the lifestyle of two vulnerable and single women traveling, Joe and Jerry learn more about the difference between the sexes, and the particular nuisances faced by women. Thus by putting on dresses, the two come to a better understanding of what it means to be a woman in a man’s world.
The Quest for Identity
Not only does cross-dressing give Joe and Jerry a better understanding of women, but it also gives them a fuller understanding of their own identities. In listening to Sugar's perspective on playboy saxophonists from the safety of his disguise as "Josephine," Joe begins to see that his two-timing ways are damaging. By living as "Josephine," he learns to be a more thoughtful and romantically sensitive man. Jerry also learns an important, if more confusing, lesson about himself. While initially, he had thrown himself into his female persona for the sole purpose of reaching a previously-forbidden intimacy with the women in the band, he eventually grows to enjoy living as a lady, and learns something about the confusing and complicated expression of his own gender.
That he so happily embodies Daphne, even when it is clear that he has become the sexual object of another man’s desire, is proof that he is in a process of learning things about his own identity that he would likely have never considered had he not cross-dressed in the first place. While his revelation of identity is somewhat confusing and inconclusive, Jerry finds a new kind of joy in accessing the "Daphne" inside him.
Crime
The opening moments of the film depict criminal activity. In the back of a hearse, Spats Columbo's men carry a coffin filled with banned alcoholic bottles. They are pursued closely by the police, and eventually the speakeasy that Spats runs gets raided by the police and its patrons are arrested.
Later, when Jerry and Joe go to pick up Nellie's car in the garage, they happen to witness a huge massacre that Spats orchestrates to get revenge on police informer Toothpick Charlie. Fleeing the scene, Joe and Jerry must escape from the criminal underworld by dressing up as women. Crime and the mafia are what set the story in motion. While intense violence and dark situations abound, crime is also treated with a light and sometimes humorous touch. The gangsters are portrayed as dim-witted thugs, and when Little Bonaparte makes a speech at the "convention," he talks about organized crime as though it were a regular corporation. Billy Wilder wants his mobster villains to be scary and intimidating, but he also wants them to be buffoons, characters the viewer can laugh at.
Wealth & Class
Joe and Jerry's first issue is that they are broke. They have no money, they are behind on their rent, and they disagree about how to spend their first paycheck from working as musicians at the speakeasy. This establishes that the question of money, how to earn it or where to find it, is at the center of the narrative. When Joe and Jerry then join the all-female band, it becomes apparent that Sweet Sue's group is not just about making music and gigging. Indeed it is a kind of matchmaking operation: the band travels to Florida, a hotbed for bachelor millionaires, in order to give its members opportunities to marry well and find security. Sugar, in particular, hopes to find a gentle bespectacled millionaire to take care of her, instead of the usual lowlife saxophone players who leave her out to dry. To her, money is also synonymous with class and decency. In order to win her over, Joe poses as a wealthy man, affecting a phony accent and using Osgood's yacht as a setting for his wooing of Sugar. On the boat, both he and Sugar pretend to be wealthier than they actually are, and they stumble through references to their high pedigree, often to comic ends.
Marriage
The girls in Sweet Sue's band are not only interested in wealth, but also in a broader security, through the institution of marriage. They don't just want to get the millionaires' money, they want to marry them too. Indeed, Jerry gets so wrapped up in the drive towards marriage, that he becomes convinced that he ought to marry Osgood, even though he is a man, and that is technically not legal. The prospect of marriage is so appealing that Jerry forgets his sex in favor of the dream of getting hitched. In this context, Jerry's interest in marriage is explicitly linked to money and wealth, and he pleads with a skeptical Joe, "Joe this may be my last chance to marry a millionaire." The dream of marrying a millionaire is such an enticing one that Jerry gets swept up in it. The dream stays alive up through the very end of the movie. Even when he thinks the revelation of his gender will reroute Osgood's desire for marriage, Osgood seems relatively unfazed, and to the confession of Jerry's manhood simply says, "Nobody's perfect."
Pretension and Performance
The most explicit instance of performance in the film is Joe and Jerry's adoption of female clothing in order to fit in with the all-girl band going to Florida, but a number of other performances take place throughout. Notably, Joe adopts two characters; in addition to his role as "Josephine" he also performs as the heir to the Shell Oil fortune, "Junior." By pretending he is "Junior," he is able to get closer to Sugar, who has already confided in "Josephine" that she wants to meet a sweet, bespectacled millionaire. Joe adopts the persona of Sugar's ideal man, which allows him to perform in such a way that earns her trust. Sugar also performs a role in hopes of impressing and winning the love of "Junior." She pretends that she is a high society Seven Sisters college graduate and former debutante. She is actually a simple girl from Ohio, but she feels the need to pretend in order to impress Joe. The irony is, of course, that neither is actually from the high society lifestyle that they each profess to know so well, and they struggle together to piece together two less-than-convincing performances.
Heartbreak
Sugar is often heartbroken throughout the movie. When we first meet her, she is a lush; she drinks a lot because she feels used by men and she is trying to find a better life, "the sweet end of the lollipop." When she meets "Junior" she becomes optimistic about her love life, thinking that she might finally find the security she always wanted. However, when Joe and Jerry encounter Spats and realize they have to split town, "Junior" must say his goodbyes to Sugar, which leaves her heartbroken again. She starts drinking again and sings the mournful "I'm Through With Love" with Sweet Sue's band. However, when "Josephine" comes and kisses her mid-song, she falls in love again, and follows "Josephine" to Osgood's escape motorboat without even quite knowing what's really going on. Sugar may be easily heartbroken, but she is also easily swayed by an admirer.
