The purpose of this study was to investigate the differences in various fashion lifestyle segments’ perceived benefits and design preferences for outdoor clothing to improve the development of outdoor clothing. Data were collected by questionnaire from 600 subjects aged 30 years and over with experience purchasing outdoor clothing in the past year. Frequency analysis, factor analysis, cluster analysis, reliability analysis, ANOVA, and chi-square analysis were used for the data analysis. The results of this study were as follows. Four segments were identified based on fashion lifestyle: manifoldly conscious, sensation conscious, practicality conscious, and brand conscious. Perceived outdoor clothing benefits generated three dimensions, including premium brand, practicality, and functionality, and preferred image produced two factors, tasteful/refined and comfortable/casual. Significant differences were found in the purpose of purchasing outdoor clothing, perceived benefit, and image and t-shirt pattern design preference among the segments. The manifoldly conscious group had a higher tendency to pursue various benefits and images of outdoor clothing and to prefer t-shirt textile designs with foulards and stripes. The sensation conscious group considered fashion and individuality in daily life but not in outdoor clothing. The practicality conscious group showed a preference for simple and casual styles with functionality and foulard patterns for t-shirts. The brand conscious group tended to prefer a striking design to functionality. This study is expected to be used as preliminary data for merchandising planning of outdoor clothing.