Lolita, the doll-like Victorian and Rococo costumes decorated with ruffles and lace, was a Japanese born youth subculture around the 1980s. Lolita has appeared and developed in Hong Kong since it was first introduced from Japan nearly two decades ago until today. It has grown unexpectedly from an insignificant to a burgeoning fashion craze internationally. This paper explores the development of Lolita phenomena in Hong Kong from the postmodern historical and social cultural points of view. In order to provide the use of terminologies and fundamental concepts of this global subculture, it firstly illustrates the background about Lolita subculture and how it has been defined, understood and analyzed by scholars from different aspects. By assembling and examining ethnographic data from interviews and materials from online resources, this research observed and evaluated that there are three major epochs of Lolita subculture development in Hong Kong namely: the Justice Epoch (2002-2005); LO Epoch (2005-2010) and HK Lolita Epoch (2010-present). It concludes that the development of Hong Kong Lolita has a strong connection with the transformation of media culture nexus.