The use of telemonitoring solutions via wearable sensors is believed to play a major role in the prevention and therapy of physical weakening in older adults. Despite the various studies found in the literature, some elements are still not well addressed, such as the study cohort, the experimental protocol, the type of research design, as well as the relevant features in this context. To this end, the objective of this pilot study was to investigate the efficacy of data-driven systems to characterize older individuals over 80 years of age with impaired physical function, during their daily routine and under unsupervised conditions. We propose a fully automated process which extracts a set of heterogeneous time-domain features from 24-hour files of acceleration and barometric data. After being statistically tested, the most discriminant features fed a group of machine learning classifiers to distinguish frail from non-frail subjects, achieving an accuracy up to 93.51%. Our analysis, conducted over 570 days of recordings, shows that a longitudinal study is important while using the proposed features, in order to ensure a highly specific diagnosis. This work may serve as a basis for the paradigm of future monitoring systems.