Early 20th century women’s fashion increasingly included the trope of “borrowing” – a trend that translated into women appropriating styles previously reserved for other subjectivities (children, men, athletes, blue-collar workers, etc). These borrowed fashions engaged an ambiguous semiotics that enabled multiple “readings” (linking a specific fashion to the demographics of a specific subjectivity) to exist simultaneously, and in some cases provided the occasion for opposite readings to exist simultaneously. This dissertation surveys a series of examples found in literature and popular culture during the early 20th century (focusing primarily on the 1920s and 1930s), analyzing the ways these “borrowed” women’s fashions collectively create a semiotic mechanism that fluidly negotiates the shifting terrains of gender representation and sexual desire – at some intervals easing cultural resistance to “transgressive” genders and desires, and in other instances underscoring previously existing regimes of heteronormative conformity.