Historically, black women’s hair has been a site where power and social relations are defined. In Puerto Rico, cultural production has been critical in perpetuating as well as in contesting the prevailing white European ideal of beauty and its impact on women’s hairstyling practices. Nevertheless, the link between aesthetic preferences and the wish to emulate white culture has been questioned in recent decades. Although not denying the persistence of racial prejudice, current historical, anthropological, and sociological studies suggest that the widespread adoption of straight hair as a model has altered its original association with whiteness, transforming it into a fashion that responds to a non-white ideal of beauty. Taking into consideration these new interpretations, this article focuses on Carmen Montañez’s novel, Pelo bueno, pelo malo. It argues that Montañez’s novel presents a complex scenario that discards the traditional shame/pride opposition ascribed to the act of hair straightening without ignoring the prejudices against Afro-Puerto Ricans.