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Understanding generational differences is basic to marketing fashion items to different generations. A company that can understand these differences will be able to create better products that speak to generations and learn how to better advertise and market to these generations. This paper represents findings of 453 surveys from members of Generation X and Generation Y, mall observation and industry interviews. It examines the motivations of each generation for purchasing fashion related items and concludes by explaining reasoning for these differences and gives suggestions to better reach these markets. Results indicate that marketers must learn the overall perception that each generation has of itself, and market based upon these views. In addition, results indicate that despite the different needs and wants a generation may have while they are young, every generation will eventually need and want the same kinds of items.