The design of a product is the first impression that a company makes on a consumer. A good design can attract consumers to the product, portray the company’s brand, and add value to the product. Therefore, the exterior design of a product is imperative to the perception of the product, and overall success in the market. In the crowded global wine industry, consumers usually judge the wine solely by its label. For a new generation of consumers, the millennial generation, it is imperative to understand their preferences in these labels. Looking at modern and classically designed labels, this study investigates what influences the millennial generation’s preference of label design. Qualitative and quantitative data from a wine tasting finds that the millennial generation’s initial visual perception is driven by their previous experience with wine, while their actual preference is driven by unconscious design likability.