Absorption and magnetic circular dichroism (MCD) spectra have been measured and theoretically simulated for a series of palladium octaethylporphyrins substituted at the meso positions with phenyl groups (n = 0-4). Analysis of the spectra included the perimeter model and time-dependent density functional theory (TDDFT) calculations. With the increasing number of phenyl substituents, the molecule is transformed from a positive hard (ΔHOMO > ΔLUMO) to a soft (ΔHOMO ≈ ΔLUMO) chromophore. This is manifested by a drastic decrease of the absorption intensity in the 0-0 region of the Q-band and by the strongly altered ratio of MCD intensities in the Q and Soret regions. Such behavior can be readily predicted using perimeter model, by analyzing frontier orbital shifts caused by various perturbations: alkyl and aryl substitution, insertion of a metal, and deviations from planarity. TDDFT calculations confirm the trends predicted by the perimeter model, but they fail in cases of less symmetrical derivatives to properly reproduce the MCD spectra in the Soret region. Our results confirm the power of the perimeter model in predicting absorption and MCD spectra of large organic molecules, porphyrins in particular. We also postulate, contrary to previous works, that the isolated porphyrin dianion is not a soft chromophore, but rather a strongly positive-hard one.