The New Silver Generation, which includes retired baby boomers, is eschewing traditional lifestyles, remaining socially and economically active, and striving to enjoy their lives. It is necessary to understand the preferences, sensibilities, and fashion propensities of such individuals. Thus, this study analyzed the New Silver Generation’s fashion color preferences and proposed fashion color scheme guidelines that could be used in the fashion industry. First, surveys were conducted in people of the New Silver Generation aged from 55 to 65 years. The survey questions included the following: fashion color preferences, fashion sensibility and taste preferences, fashion interests, lifestyle, and demographic background. Second, the survey was conducted to identify differences in color preferences based on respondents’ fashion interests and lifestyles. Next, to compose color palettes for the survey, 45 colors from the Munsell color system were chosen at random. The major research results were as follows: It was shown that socializing- and health-preferring individuals wore achromatic color, leisure-preferring individuals wore P color, and self-preferring individuals wore B color. The commonly worn colors were achromatic colors. After the age of 55 years, health- and leisure-preferring individuals often wore R color and RP color, respectively. Thus, this study proposed a color scheme arrangement that used achromatic colors, such as black and white, as the main colors list for the four lifestyle types.