Transportation systems have significantly evolved over the past century, prompting the development of predictive, analytical, and optimization models. Since the 1950s, the trajectory of transport modeling has been shaped by various philosophies of science, influencing assumptions, methodologies, and outcomes. This research advocates for a contemporary philosophy of science that aligns more effectively with current modeling practices, recognizing them as linguistic activities within the broader framework of transport planning. The paper introduces three alternative perspectives—metaphorical, narrative, and aesthetic—as avenues for reimagining transport models. Despite the shift from deterministic to complex systems-based methodologies, existing models encounter challenges in addressing subjective aspects of human behavior within transportation systems. Employing storytelling, the narrative approach enhances communication by integrating subjective elements into transport planning. Meanwhile, the aesthetic approach, which emphasizes visual representation, underscores the importance of design and aesthetics in shaping stakeholder perceptions. The research concludes by proposing future research directions that incorporate formal philosophical thinking into transport modeling research and practice, highlighting the potential of these models to enhance the economic aspects of transportation systems.