American advertisers consistently advanced the aspirational class status of owning cars for women. With imagery ranging from the Cinderella fairy tale to European landmarks, the promise of achieving a high status through the purchase of a car beckoned. A small case study of Cadillac's luxury advertising explores how the company used prestige to attract both women and African Americans and found loyalty. However, their car dealers fundamentally disdained both groups of consumers. This article examines how automotive advertisers encouraged women to strive to boost or maintain their family's class status and shifted their idealized portrayals from women taking drives in the country and playing golf to showcasing women transporting family members to the train station, school, and sporting events. Drawing on research from the Ford archives, popular magazines, and transportation libraries, this article analyzes the tropes advertisers employed to signify the wealth of the car owner.