To improve consumers’ online shopping experiences, companies invest in the visual design of their websites. Although some studies show that visual design exerts a positive influence on consumer reactions, other studies do not confirm that influence. This research is aimed at exploring those contrasting findings by investigating two boundary variables (website use and user expertise) that delimit the scope of the positive influence of visual design on consumer intentions towards using and recommending e-commerce websites. Two preliminary studies (Study A and Study B) investigate the level at which visual design is mentally construed. The two main studies (Study 1 and Study 2) test our research hypotheses. The Study 1 results reveal that visual design exerts different effects on individuals’ intentions depending on when the site is evaluated (before vs after use). Study 2 provides greater insight into the role of visual design after actual use of the website by considering the moderating role of user expertise. Those findings lead to the formulation of concrete recommendations about how e-retailers can create more engaging experiences.