Aerodynamic drag is one of the two principal external sources of energy loss in on-road vehicles – the other being rolling resistance – and it critically affects the range of battery-electric and fuel cell-electric vehicles. To ensure accurate early-stage analysis such as vehicle range prediction and sizing of energy storage and powertrain components, it is essential to incorporate realistic representations of air resistance. Despite its importance, due to limited data availability air resistance is often simplified using zero crosswind and "nominal air conditions", which tend to underestimate the actual energy required to overcome aerodynamic drag. This approach also fails to capture the variability introduced by changing environmental conditions, leading to significant discrepancies in energy consumption and, consequently, vehicle range. As a result, evaluating system robustness and conducting meaningful trade-off analyses between different vehicles or vehicles configurations becomes challenging. This study demonstrates how publicly available meteorological data can be utilized to quantify long-term variations in aerodynamic drag. By analyzing multiple years of weather observations, we derive realistic distributions of aerodynamic energy losses – capturing not only mean values but also the full range of variability. These distributions enable probabilistic modeling of vehicle performance, thereby supporting robust system design and informed trade-off decisions across various levels of vehicle architecture. To demonstrate this, we compare two different tractor/semitrailer configurations.