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Throughout the first half of twentieth century, the act of smoking transitioned from being an exclusively male to a predominantly female practice. Indeed, by the end of the twentieth century merely being female was considered a serious risk to developing a smoking habit. This cultural shift is reflected in contemporary cigarette advertising, in which women begin as attractive accessories to male smokers and gradually become depicted as smoking independently. These advertisements were actively engaged with the social worlds of the women they targeted, drawing upon their contemporary concerns and values, namely those of women’s liberation and an increased attention placed upon body image. This paper argues that the majority of this male to female advertising shift took place between 1920 and 1940, during which advertisements adapted their imagery to accommodate smoking as paradoxically both a powerful symbol of liberated femininity and as a means of conforming to the image of the attractive modern woman.