The present study examines how gaze behavior relates with users’ expertise in evaluating the visual appeal of a website. We adopt four facets of visual aesthetics (i.e., simplicity, diversity, colorfulness, craftsmanship) and explain how ones’ expertise may change the way he or she looks at a high or low appealing website. We employ eye-tracking techniques to capture users’ gaze behavior while looking at high and low appealing e-commerce websites, on a sample of 23 users with previous experience in e-commerce. The findings show that expert users’ make more careful observations, have a deeper cognitive processing, demonstrate less anticipation, along with more local processing and engagement with the task than novices. Also, gaze behavior remains the same for both low and high appealing websites. The study contributes by providing evidence on how to capture and use gaze data from experts to train new and inexperienced users to have more accurate judgements about the aesthetics of websites, and thus improving both user experience and website design.