The incidence and disease burden of arthropod-borne flavivirus infections have dramatically increased during the last decades due to major societal and economic changes, including massive urbanization, lack of vector control, travel, and international trade. Specifically, in the case of dengue virus (DENV), the geographical spread of all four serotypes throughout the subtropical regions of the world has led to larger and more severe outbreaks. Many studies have established that recovery from infection by one DENV serotype provides immunity against that serotype, whereas reinfection with another serotype may result in severe disease. Pre-existing antibodies thus play a critical role in controlling viral infection. Both neutralization and enhancement of DENV infection by antibodies are thought to be related to the natural route of viral entry into cells. In this review, we will describe the current knowlegde on the mechanisms involved in flavivirus cell entry and discuss how antibodies may influence the course of infection towards neutralization or enhancement of viral disease.