The incidence of respiratory and cutaneous allergic disorders may be variable if we consider work activity. These disorders are reported in the current literature to have a relevant psychosomatic involvement. The aim of the study was to submit a survey on the self-reported occurrence of allergic respiratory and cutaneous diseases in outdoor and indoor workers to verify the onset or exacerbations of such pathologies, encourage surveillance, and suggest the need for further studies. Two groups of workers were compared when exposed and not exposed to air pollutants. An outdoor population of motorway toll collectors (153 workers; M: 58.03 years old, SD: 6.1; and female prevalence of 66.01%) and an indoor group of office employees (59 workers; mean age 54.44 years, SD: 8.50; and male prevalence of 61.02%) entered the study. The results of three multivariate analyses of the obtained data, investigating contributions of external factors, including age, sex, smoking habits, working type, and seniority, on allergic conditions were significant in both workers’ groups. The findings highlighted that age and smoking habits were significant contributors to allergic conditions, both independently and in combination with other factors, such as sex and working type. The data suggest the presence of phenomena related to different etiological domains, as already reported in the literature. Through the collection of these data, it was possible to highlight the need to analyze clinical signs from different perspectives.