Women aged between 36 and 55 are the main players in the cosmetics market in Taiwan in recent years. Particularly, the sector of anti-ageing cosmetics has grown continually with the support of women at the ages, who have stronger purchasing power than others. Furthermore, the changes of the channel structure in Taiwan have an impact on cosmetics consumption. Department stores have been the leaders of the high-end cosmetics market for a long time. Nevertheless, Taiwanese middle-aged women no longer only purchase cosmetics products in the department stores, but also shop around the pharmacy chain stores, like Cosmed, Poya and Watsons, which expand rapidly in Taiwan recently, buying OTC (Over-the-counter) cosmetics brands and products. It is convenient for women to attach with cosmetics products since the widespread shops available for consumers to pop in and consume a wide range of cosmetics products with more affordable prices (Kantar Worldpanel, 2013). The current research examines the cosmetics shopping and consumption of middle-aged women in the Taiwanese cultural context. The phenomenological interviews were conducted with a purposive sampling with 6 Taiwanese middle-aged women ranging in age from 40 to 60, who used cosmetics on a daily basis, varied in duration, between 1 to 2 hours. The sample size is kept deliberately small as phenomenological interviews are designed to elaborate the richness (Baker et al., 1992) of individuals’ lived experiences, feelings and perceptions of cosmetics consumption. Each interview was conducted online using the social media, Skype, through a webcam. The purpose of the interview was described to the informants as an exploration of women’s cosmetics consumption and how it affected their experiences in their daily lives. They were encouraged to share their own experiences freely. The unstructured interviews started with a question, “What comes to your mind when speaking of cosmetics?” enabling participants to start the dialogue with their most familiar topics and be free to define the meanings of cosmetics in their own words (Liu et al., 2012). In the process of data analysis, 6 principal themes emerged to give more explanations in detail of how middle-aged women in Taiwan strategically manipulate cosmetic shopping to construct, maintain, change, and give meanings to the sense of self in transformational levels during their lifetime course. In addition, due to the widespread of pharmacy stores in recent days, it is found that the middle-aged women’s had changed their shopping behaviours in accordance with the change of retail stores. For example, Karen likes to shop around the pharmacy stores looking for open counter brands which are made in Japan and buying products with the signs showing that are ranked number 1, instead of shopping at the department stores, where she used to go. Moreover, Amy also likes to go to the pharmacy stores which are close to where she lives. There are many new-opened stores, such as Cosmed, Watsons, and Poya rapidly expanded in the rural area that make it more convenient for residents to shop in. She also prefers to buy facial cleansing products which are made in Japan and ranked number 1. As the structure of channel and lifestyle have changed with time, consumers’ cosmetics consumption is changing as well. The research finds that wearing cosmetics has become habits for the Taiwanese women aged between 40 and 60 since they have been using cosmetics for more than 20 years. The meaning behind their “used-to habits” with cosmetics is that consumer’s possessions - cosmetics, have become their extended self and being strategically manipulated to accompany them experiencing through every path of their lives, including pursuing their ideal, hoped-for possible selves, escaping from their negative, feared possible selves, managing their relationship with the social self, and developing their past-present-future self within the historical context.