Society recognizes the role of clothing as a communicator of information during social interaction and as an aid in the establishment of self-identity. As an adolescent builds self-identity, self-esteem and use of clothing to affect its enhancement become important aspects of his/her development. This study sought to (1) determine if there were differences in the importance of clothing comfort in three situations (social, school, and leisure) among adolescents in a metropolitan city (500,000 SMSA), and (2) to determine if there was a relationship between the rating on the importance of clothing comfort and the level of self-esteem in social, school, and leisure situations. The importance of clothing comfort was measured using the Clothing Comfort Dimensions, Importance by Situation, and self-esteem was measured using the Sliding Person Test of Self-Esteem. One hundred ninety-seven female junior high students from a metropolitan city responded to a self-administered questionnaire. Statistically significant interactions were found among the three situations (social, school, and leisure) in each of the three dimensions (physical, social, and psychological) for the importance of clothing comfort. Adolescents acknowledge clothing comfort as being more important in social and school situations than in leisure, and they reflect limited differences in importance of clothing comfort in social or school situations. No significant differences were found among self-esteem scores across the five groups of individuals who placed the level ofclothing comfort importance as from Very Important to Very Unimportant. For this group of adolescents, self-esteem was not related to situational clothing comfort.