Objective: With aging, gait becomes more dependent on executive functions, especially on switching abilities. Therefore, cognitive-motor dual-task (DT) paradigms should study the interferences between gait and switching tasks. This study aimed to test a DT paradigm based on a validated cognitive switching task to determine whether it could distinguish older-old adults (OO) from younger-old adults (YO). Methods: Sixty-five healthy older participants divided into 29 younger-old (<70 years) and 36 older-old (≥70 years) age groups were evaluated in three single-task (ST) conditions as follows: a cognitive task including a processing speed component [Oral Trail Making Test part A (OTMT-A)], a cognitive task including a switching component [Oral Trail Making Test part B (OTMT-B)], and a gait evaluation at normal speed. They were also evaluated under two DT conditions, i.e., one associating gait with OTMT-A and the other associating gait with OTMT-B. Cognitive and gait performances were measured. The comparison of cognitive and gait performances between condition, logistic regression, and receiver operating characteristic (ROC) analyses were performed. Results: The cognitive and gait performances were differently affected by the different conditions (i.e., ST, DT, OTMT-A, and OTMT-B). The OTMT-B produced higher interference on gait and cognitive performances. Moreover, a higher number of errors on the OTMT-B performed while walking was associated with the older-old age group. Conclusion: Using validated cognitive flexibility tasks, this DT paradigm confirms the high interference between switching tasks and gait in older age. It is easily implemented, and its sensitivity to age may highlight its possible usefulness to detect cognitive or motor declines.