Objective: Observational studies on the association among systemic/general and oral cavity indices, tooth loss, periodontal conditions, and socioeconomic inequalities are to be still performed in the population of Southern Europe. This study aims to determine the extent of this relationship among Italian healthy adults 50 years of age and above. Materials and Methods: Socioeconomic and lifestyle characteristics, cardiovascular indicators, and systemic indices were examined by contrasting the dental indices among adult people of Northern Italy. Data were processed through correlation analysis, and multivariate analysis was carried out using seemingly unrelated regressions. Results: A total of 118 adults 50 years of age and above, after anamnesis, underwent systemic and dental examination. Their socioeconomic status was found to be inversely associated only with smoking and dental parameters. Unexpected outcomes between lifestyle and risk factors were detected. The statistical analysis showed an uneven correlation among dental indices and between those indices and the socioeconomic status, such as, a periodontal condition, apparently free from influences, unusually became worse as the socioeconomic status enhanced. Conclusions: The study outcomes indicate a relationship between tooth loss and conservative endodontic therapy, but they result in alternative choices. Nevertheless, the socioeconomic status has an inverse relationship with tooth loss and conservative endodontic therapy, but a direct relation with worsening of the periodontal condition. This pilot study highlights a need for the public health administration to adopt a socioeconomic assessment not only based on the household income, but also to accordingly improve its therapeutic course.