Consumers often want to be cool and marketers attempt to capitalize on this desire by positioning their brands as cool. Despite this, little is known about how coolness originates or when coolness influences consumer behavior. Using an experimental approach, my research addresses both of these gaps in the literature. I identify an overlooked origin of coolness: autonomy from mainstream society. My studies suggest that people and brands can become cool by displaying bounded autonomy, which is typically inferred from displays of rebellion and uniqueness. Autonomy has a curvilinear relationship with perceived coolness, and the level of autonomy considered cool depends on the ideological orientation of the consumer. Consumers higher in counterculturalism, the endorsement of an ideology centered on the belief that society imposes a repressive force that leads to widespread conformity, will consider higher levels of autonomy cool compared to consumers lower in counterculturalism. Additionally, my research suggests two reasons why consumers desire coolness: coolness influences social status and signals autonomy. Although cool brands can signal desired identity traits, like status and autonomy, consumers do not always prefer brands they consider cooler. Desire for cool brands is depends on dispositional and contextual factors that influence consumers’ need to express an autonomous identity. Cool brands are more likely to be preferred to uncool brands by consumers with a high need for uniqueness, when the brand will be consumed in the presence of a more countercultural audience, and when the consumer’s identity as an autonomous individual has been threatened.