In this study, based on the perception of older adults, fuzzy positioning of healthcare wearables and impacts of differentiated product positioning on human considerations and design communication strategies are studied. Empirical researches are performed by adopting both quantitative research (248 questionnaires for clustering and regression analysis) and qualitative research (15 cases for in- depth interview). The perceptions of older adults on product positioning are divided into three types: Tech-Aid, Fash-Acc, and Fash-Tech. Results indicate that the influential human considerations for each positioning were different from each other. Through coding and storyline analysis, diverse communication strategies are found for each positioning. The outcomes for each type are as follows. For Tech-Aid, wherein older adults lay emphasis on usefulness, ease of use, and privacy, the designers can adopt a calm communication strategy by giving priority to older adults’ control power, fitting symptoms, user-friendly, and cautious interconnection. For Fash-Acc, wherein older adults focus on personal image, aesthetic appearance, and ease of use, an active communication strategy for modeling a style for elderly fashion that agrees with aesthetic appreciation and simplified operation can be adopted. For Fash-Tech, wherein older adults require to integrate usefulness, ease of use, aesthetic appearance, comfort, privacy, and self-image, a persuasive communication strategy can be used, through which designers can offer older adults more data insights and entertainment, along with data association, and in the meantime, reduce data interferences and pay attention to style modality and appropriate display with context fusion and contact comfort.