Due to recent changes in increased life expectancy, economic power and social development, the new senior generation (focusing on people in their fifties) represents a new market power with strong competitiveness. The new senior generation is the generation after the baby boomers, with characteristics that include a high-level of education, increased income, a high-level of consumption, increased assets, self-fulfillment desires and individuality. Demands in the senior fashion industry are expected to gradually increase and the underwear industry that targets the new senior generation is expected to grow rapidly. These demands will require product development for the new senior generation based on emotional and socio-cultural characteristics. The current new senior underwear market is under the process of R&D with a focus on body shape changes; however, there are limited studies on emotional and socio-cultural approaches. This study formulates a basic design plan for different age groups based on an analysis of the situation of bra wear (current inconveniences, demand and needs) by women in their fifties and over. Subsequently, a functional active bra top that considers activity and comfort was proposed for women in their fifties, an all-in-one foundation bra top that shapes the body was proposed for women in their sixties, and comfort bra tops that are comfortable and easy to put on and take off were proposed for women in their seventies and over.