The understanding of the antecedent of online purchase intentions is imperative for the growth of electronic commerce. This paper extended the technology acceptance model by three factors electronic word of mouth, online advertisement value, and attitude toward Egyptian websites, and empirically examined the proposed model among Egyptian Internet users. Furthermore, based on online purchase intention, market segmentation was conducted. A structured online questionnaire was used to collect 479 responses. Explanatory factor analysis and cluster analysis were performed using SPSS software; the structural equation modeling and hypotheses testing were examined using Amos IBM. The paper contributed by identifying the main factors shaping internet users’ intention toward online shopping in Egypt. Results revealed that perceived enjoyment had the most influence, followed by electronic word of mouth. Besides, perceived enjoyment totally mediated the relationships between online advertisement value, information usefulness and behavioral intention. Also, there was a significant negative relationship between the attitude towards Egyptian websites and the perceived risk. Three groups resulted from cluster analysis, online shoppers’ lovers, potential online shoppers, and online shoppers’ avoiders. Online shoppers’ lovers had the highest online purchase intention and the lowest perceived risk; they recorded the highest perceived enjoyment, information usefulness, perceived ease of use, and electronic word of mouth. The online shoppers’ avoiders had the lowest online purchase intention and the highest perceived risk. The potential online shoppers recorded values are not as high as the lovers nor low as the avoiders. The findings of this study provide important information to marketers about the behavioral characteristics of each consumer segment.