The Y generation born between 1981 and 1995 is the largest consumer group in the United States. This study is to provide an insight of understanding Y generation’s decision factors of purchasing Jeans and the fit issues. This study investigated their purchasing decisions factors, including fit, cost, brand, color, and the media/internet influences. It is revealed that the Y generation might have access to the internet, but they still rely more on their peers and savvy skills to decide what they purchase. They preferred to shop from the land based retail stores rather than the internet. The fit was the most important factor of their purchasing decision, but less concerns of the brand. In this study, 87% of them chose “fit” as the reason to buy a pair of jeans. Fit problems were related to the price category. This study suggests apparel manufacturers should understand Y generation’s fit issues in the global market.