A typical consumer is exposed to more than 5,000 advertisements per day (Story 2015) by exposure to around 500 advertising messages before ending breakfast (Marshall, 2015), and it is impossible for consumers to remember most of the advertisement images and messages. Thus, one consistent yet not thoroughly investigated question for advertisers is how advertisers draw consumers' attention by differentiating their brand from competitors' brands. One suggestion from academia is making more "creative" advertising (Dahlén et al., 2008; Lehnert et al., 2014; Rosengren et al., 2013; Smith et al., 2008). However, it is still questionable the exact meaning of "advertising creativity," and the effects of creative advertising on consumer evaluation have not been fully investigated the effects of creativity in advertising evaluation by considering various boundary conditions. The objective of this research is to redefine advertising creativity, to understand how advertising creativity shapes consumers' evaluation, and how these effects are moderated by the different types of boundary conditions, such as industry category, by analyzing more than 100,000 advertising images and copies using a cutting-edge transfer learning technique. The results of the transfer learning algorithm indicate that both cognitive dimensions (e.g., novelty of image) and affective dimensions (e.g., awe and coolness) simultaneously affect the consumers' perception of the advertising creativity, and the current algorithm enables to detect of creative advertising image with 92% accuracy rate.