The goal of the study is to verify the incidence of maternal relationship styles on adolescents’ self-esteem. The research involved 285 mother-son/daughter couples. The short version of Multidimensional Self-Concept Scale (Manna, Mirisola e Boca, 2005) was admistered to a sample of 285 adolescents (122 boys, 163 girls) aged from 13 to 19 years old (mean age = 16.23 years, sd = 1.64); the Italian version of Attachment Style Questionnaire (Fossati, Feeney, Donati, Donini, Novella, Bagnato, Acquarini e Maffei, 2003), was admistered to a sample of 285 mothers. Results of a multivariate analysis of regression show that maternal secure attachment style influences positively the adolescents’ relational style; on the contrary, maternal insecure attachment style has a negative impact on adolescents’ self-worth.