Advertising, which is an important sales tool for brands to the masses, may produce lasting impressions of a company and its products. These impressions rely on a consistent message over time to maintain a brand's image. This study examines how Ralph Lauren's advertising images have changed from a country club lifestyle image to urban/hip. In addition, the study examines the increased use of nudity and sexual imagery in Lauren's advertising. The findings were obtained by content analyzing all Ralph Lauren advertisements appearing in Gentlemen's Quarterly magazine from 1980 to 2000 (N=283). The study finds that Ralph Lauren lifestyle images have become more urban/hip, and that Lauren's advertising is utilizing more nudity, sexual interaction, and homoerotic imagery. By examining Ralph Lauren's shifting brand image via its advertising, this study contributes to a greater understanding of the connection between advertising and a company's brand image.