A large series of photochromes of the spirooxazine family has been investigated using density functional theory and time-dependent density functional theory, aiming at designing molecules with an open-ring merocyanine form absorbing at the longest possible wavelength. A complete methodological assessment (basis set, solvent effects, functionals) has been performed, allowing the design of efficient multilinear regressions for two solvents (cyclohexane and toluene). These regressions allow the estimate of the absorption wavelength of open spirooxazine with an error limited to about 5 nm. The thermodynamic and spectral properties of several isomers have been considered, and it turned out that only TTC and CTC structures may appear experimentally. These structures present similar stabilities and absorption wavelengths. The impact of the auxochromic groups on the UV/vis spectra was assessed and novel promising substitution patterns have been unravelled. It is shown that using a strong push moiety on the same side of the molecule as the pull group may be an effective procedure for tuning the visible spectra. In particular, several spirooxazines with absorption wavelength predicted to be close to or larger than 700 nm are proposed.