Millennials, or Generation Y, represent one of today’s most prominent age cohorts: with their increasingly stronger purchasing power and importance in the global economic landscape, it is no wonder that marketers are striving to find new ways to appeal to the taste of this peculiar generation of consumers. Among the various modern research fields in business, one in particular is offering incredibly interesting insights to both scholars and professional marketers: the concept of nostalgia proneness in consumer behavior. While several studies examine the dynamics of this phenomenon, none of them so far examined the impact of nostalgia proneness in shopping behavior, especially examining the dynamics on a sample of Generation Y consumers. This study was conducted in order to explore the dynamics of nostalgia proneness, linking the constructs to both desire for uniqueness and shopping behavior, using the framework provided by the Consumer Styles Inventory (Sproles & Sproles, 1990). After a theoretical review on the matter, several hypotheses and a conceptual model were developed to serve as the core framework of the quantitative analysis. The data, obtained from a convenience sample of 222 respondents, were subsequently examined using several statistical techniques (ANOVA, correlation and factor analysis), with the intent to test the hypotheses and shed light on the research questions. The outcome was then presented and interpreted using both the theoretical background and other complementary relevant literature. The results showed a positive relationship between nostalgia proneness and desire for uniqueness, with both variables being further connected to several shopping traits of the Generation Y consumer. The cluster and factor analysis eventually showed patterns that could be interpreted using the theory of hedonic and utilitarian shopping motivations.