This study examined the relationships between consumers’ skill, perceived challenge, online flow, brand experience, and brand loyalty in the context of online shopping on an apparel brand’s website. Data were collected using an online survey with a national sample of 400 female adults (age 20-34). Respondents were asked to perform an online browsing task on an existing brand’s website randomly assigned to them and answer questions about the task. The results from structural equation modeling analysis show that more skillful consumers are more likely to reach a state of online flow on a brand’s website, and the relationship between skill and online flow was moderated by the level of challenge felt by consumers about the given task. Further, online flow positively influenced sensory and affective brand experiences, which in turn led to brand loyalty. Theoretical and managerial implications of the findings are discussed along with limitations and recommendations.