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<b>Background/Objectives:</b> Socioeconomic stressors, such as financial strain, rising living costs, and perceived price burden, have gained relevance in the post-pandemic period and may adversely affect adolescent mental health. This study examined the association between subjective financial stress and symptoms of depression, anxiety, and emotional/behavioral difficulties among adolescents in Northern Italy. <b>Methods:</b> Data were obtained from the 2025 Corona and Psyche South Tyrol (COP-S) population survey. A total of 2554 adolescents aged 11-19 years and their parents participated; 1598 adolescents provided complete data for analyses of socioeconomic stressors (parent-reported Family Affluence Scale III, adolescent self-reported and parent proxy and self-reported burden due to price increases). Mental health outcomes included depressive symptoms (PHQ-2), generalized anxiety (SCARED-GAD), and emotional/behavioral difficulties (SDQ). Associations were assessed using chi-square tests, Kendall's tau correlations, and two-factor ANOVA models. <b>Results:</b> Elevated depressive symptoms were present in 10.7% of adolescents, emotional/behavioral difficulties in 13.9%, and anxiety symptoms in 27.9% of adolescents. Female adolescents consistently showed higher symptom levels in all domains. Self-reported financial burden was the strongest and most consistent correlate of mental health problems, demonstrating small-to-moderate positive correlations with depressive symptoms (τ = 0.20, <i>p</i> < 0.001), emotional/behavioral difficulties (τ = 0.14, <i>p</i> < 0.001), and anxiety (τ = 0.25, <i>p</i> < 0.001). Parent-reported burden showed weaker and less consistent associations, and the Family Affluence Scale III was not significantly related to any of the mental health outcomes. ANOVA models indicated that adolescents' own perception of financial burden significantly predicted anxiety levels in both age groups (11-14 and 15-19 years), whereas discrepancies between adolescent and parent burden perceptions were particularly relevant among younger adolescents. <b>Conclusions:</b> In this affluent European region, subjective financial strain, especially adolescents' perception of burden due to rising prices, is a stronger determinant of depressive symptoms, anxiety, and psychosocial difficulties than parental burden reports or structural affluence indicators. Adolescents, especially females, appear to be particularly vulnerable. These findings underscore the importance of addressing subjective financial stress in adolescent mental health and public health strategies.