Each charge method operates on its own scale (although atomic contributions do sum to total molecular charge) and all types have been used for various applications. In this work, we explore the ability of various charge models from Classes II-IV (what we term a bottom-up description) to describe empirically determined (i.e., top-down) Hammett parameters. While important general considerations -for example, regarding the more stable performance of Hirshfeld or NPA charges vs. Mulliken for different basis set sizes -have been reported previously, less specific information is available to guide the choice of computational protocol in describing macroscopic electronic parameters. Our quantitative comparisons against Hammett parameters addresses this need.