This series, the bulk of which dates from 1897 to 1908, consists of compositions, grade books, notebooks, scrapbooks, printed material, and ephemera, including paper dolls and a Parisian board game. These materials document the type and quality of Helen Clay Frick's academic training, her youthful interests and recreational pursuits, and to a lesser extent, give some insight into her religious and physical education. They detail Helen Clay Frick's studies in foreign languages, music, mathematics, history, literature, ethics, and other subjects, and give a sense of her relationship with her parents and her Swiss governess, Marika Ogiz.

The bulk of the series consists of notebooks on school-related topics, and date from Helen Clay Frick's studies in both Pittsburgh and New York. Early notebooks often contain corrections and comments by Mlle. Ogiz. In addition to these evaluations, Ogiz also compiled grade books, which provide a weekly overview of Helen Clay Frick's performance, conduct, and attendance. The grade books contain lists of topics studied, indicate the employment of additional tutors (e.g. Harriet T. Duff and piano teacher Mr. McGinnis), and note non-instructional days due to holidays, travel, or illness. These books were regularly shared with Helen Clay Frick's parents, as indicated by frequent comments from her father, and occasional contributions by her mother. Later grade reports issued by the Spence School are collected into a bound volume bearing an inscription from Henry Clay Frick to his daughter. In addition to the notebooks and grade books, this series also contains a scrapbook dating from Helen Clay Frick's time at the Spence School. This scrapbook commemorates her graduation, with details about her class, a class portrait, signatures of her teachers, programs, a class "prophecy," and calling cards and invitations from friends. One loose program and one within the scrapbook document school productions for the benefit of charity.

Helen Clay Frick's 1908 graduation from Spence marked the end of her formal education, and she made her debut in society later that same year in Pittsburgh. Documents and memorabilia from that event include a dance card, guest lists, and a scrapbook with images, clippings, and notes. The scrapbook also contains a few scattered items from the year following Miss Frick's debut, notably clippings about the Iron Rail Vacation Home, her first philanthropic endeavor, located in Wenham, Mass., and notices regarding the engagement and wedding of her childhood friend, Virginia Frew, to Thruston Wright.