We present two possible criteria quantifying the degree of classicality of an arbitrary (finite dimensional) dynamical system. The inputs for these criteria are the classical dynamical structure of the system together with the quantum and the classical data providing the two alternative descriptions of its initial time configuration. It is proved that a general quantum system satisfying the criteria up to some extend displays a time evolution consistent with the classical predictions up to some degree and thus it is argued that the criteria provide a suitable measure of classicality. The features of the formalism are illustrated through two simple examples.