This paper adds to the growing empirical evidence on the importance of habits in governing human behavior, and sheds new light on individual inertia in relation to transportation behavior. An enriched perspective rooted in Veblenian evolutionary economics (VEE) is used to construct a theoretical framework in order to analyze the processes at play in the formation and reinforcement of habits. The empirical study explores more specifically the synchronic processes strengthening the car-using habit. In addition to underlining the shortcomings of a ‘decision theory’ perspective to address urban transportation behaviors, we find that synchronic habits can have a significant effect on behavioral inertia. Our results suggest the existence of positive feedback between the development of synchronic habits, qualitative perceptions of driving times, and reinforcement of the car-using habit. The paper points out also that the diachronic dimension of habits would constitute another promising domain for further research on behavioral inertia in transportation.