This study aims to analyze product samples of convergence of fashion and technology, as convergence is a major trend in the age of digital paradigm, and to propose desirable directions of development for technology convergence in fashion design in the future. With bibliographic research as well as internet search of the cases of development and commercialization of convergence of fashion and technology from the 1960s, when wearable computers were first introduced as an early development form of convergence, to the present, it becomes possible to classify these cases into three groups: functionally oriented one, aesthetically oriented one, and one that combines function and aesthetics. The pros and cons of each group of these cases are discussed and an evolutionary trend is observed from the earlier stage of convergence with functionally oriented cases which tried to achieve specific purposes of the time to the later stage of convergence with emphasis on both function and aesthetics which reflects the sensitivity of the general wearers. When three groups are plotted in the positioning map with one axis of function-aesthetics and the other of industry-fashion designer, however, all three are located outside of the two axes, suggesting these elements are not very well combined. In order for the products of the fashion-technology convergence in the future to receive favorable response from the consumers, it is necessary for the fashion industry to develop a close collaboration with companies of digital technology and the convergence products not only will have to provide functional benefits of the new technology but also to satisfy the aesthetic demands of the wearers.