The growing concern on adolescent mental health calls for proactive early detection and intervention strategies. There is a recognition of the link between digital phenotypes and mental health, drawing attention to their potential use. However, the process of collecting digital phenotype data presents challenges despite its promising prospects. This study aims to develop and validate system concepts for collecting adolescent digital phenotypes that effectively manage inherent challenges in the process. In a formative investigation (N=34), we observed adolescent self-recording behaviors and conducted interviews to develop design goals. These goals were then translated into system concepts, which included planners resembling interfaces, simplified data input with tags, visual reports on behaviors and moods, and supportive ecological momentary assessment (EMA) prompts. A proof-of-concept study was conducted over 2 weeks (n=16), using tools that simulated the concepts to record daily activities and complete EMA surveys. The effectiveness of the system was evaluated through semistructured interviews, supplemented by an analysis of the frequency of records and responses. The interview findings revealed overall satisfaction with the system concepts, emphasizing strong support for self-recording. Participants consistently maintained daily records throughout the study period, with no missing data. They particularly valued the recording procedures that aligned well with their self-recording goal of time management, facilitated by the interface design and simplified recording procedures. Visualizations during recording and subsequent report viewing further enhanced engagement by identifying missing data and encouraging deeper self-reflection. The average EMA compliance reached 72%, attributed to a design that faithfully reflected adolescents' lives, with surveys scheduled at convenient times and supportive messages tailored to their daily routines. The high compliance rates observed and positive feedback from participants underscore the potential of our approach in addressing the challenges of collecting digital phenotypes among adolescents. Integrating observations of adolescents' recording behavior into the design process proved to be beneficial for developing an effective and highly compliant digital phenotype collection system.