The view that the large red shifts seen in the UV-visible absorption bands of peripherally crowded nonplanar porphyrins are the result of nonplanar deformations of the macrocycle has recently been challenged by the suggestion that the red shifts arise from substituent-induced changes in the macrocycle bond lengths and bond angles, termed in-plane nuclear reorganization (IPNR). We have analyzed the contributions to the UV-visible band shifts in a series of nickel or zinc meso-tetraalkylporphyrins to establish the origins of the red shifts in these ruffled porphyrins. Structures were obtained using a molecular mechanics force field optimized for porphyrins, and the nonplanar deformations were quantified by using normal-coordinate structural decomposition (NSD). Transition energies were calculated by the INDO/S semiempirical method. These computational studies demonstrate conclusively that the large Soret band red shifts (similar to40 nm) seen for very nonplanar meso-tetra(tert-butyl)porphyrin compared to meso-tetra(methyl)porphyrin are primarily the result of nonplanar deformations and not IPNR. Strikingly, nonplanar deformations along the high-frequency 2B(1u) and 3B(1u) normal coordinates of the macrocycle are shown to contribute significantly to the observed red shifts, even though these deformations are an order of magnitude smaller than the observed ruffling (1B(1u)) deformation. Other structural and electronic influences on the UV-visible band shifts are discussed and problems with the recent studies are examined (e.g., the systematic underestimation of the 2B(1u) and 3B(1u) modes in artificially constrained porphyrin structures that leads to a mistaken attribution of the red shift to IPNR). The effect of nonplanar deformations on the UV-visible absorption bands is then probed experimentally with a series of novel bridled nickel chiroporphyrins. In these compounds, the substituent effect is essentially invariant and the amount of nonplanar deformation decreases as the length of the straps connecting adjacent meso-cyclopropyl substituents decreases (the opposite of the effect observed for conventional strapped porphyrins). Several spectroscopic markers for nonplanarity (UV-visible bands, resonance Raman lines, and H-1 NMR resonances) are found to correlate with time-averaged deformations obtained from an NSD analysis of molecular dynamics snapshot structures. These results suggest that UV-visible band shifts of tetrapyrroles in proteins are potentially useful indicators of changes in nonplanarity provided other structural and electronic factors can be eliminated.