The present study focused on the relationships between idiosyncratic sextyping and self-esteem. Idiosyncratic, feminine, masculine, and nonstereotyped sets of self-attributes, termed self-images (SI), rather than conventional masculinity, femininity and their interaction (androgyny), were used Findings from two studies with two groups of 337 Israeli early adolescents boys and girls, and 280 male and female university students, using two instruments of sex-typed self-attributes (newly devised Self-Related Self-Image Scale and Spence Personal Attributes Questionnaire) and based on idiosyncratically defined sex images, supported our hypotheses. The findings showed that males' self-esteem was predicted significantly by their masculine SI, that females' self-esteem was predicted significantly by their nonstereotyped SI, and that the feminine SI predicted significantly the self-esteem of neither. Findings based on conventional sex role orientation scores supported former findings of significant relationships between masculinity and male and female self-esteem. The results showed that the self-esteem of male students, but not that of boys, was significantly predicted by their nonstereotyped SI too. Partial support was found for the hypothesis that more females than males are likely to redefine conventional masculine attributes as nonstereotyped. The whole set of findings were interpreted as indicating that self-esteem is dependent on socially rewarded and self-synchronized sex-typed attributes.