Bathochromical shifts in the UV-vis absorption (and emission) spectra and reduced molecular sizes are two desirable features of organic dyes in many applications, i.e., live-cell fluorescence imaging and solar cells. Yet, these two features are often viewed as contradictory requirements as expanding the π-conjugation is one of the most widely used methods for prompting this redshift. Interestingly, it has been reported that linking a methine-quinoidal unit can result in a significant redshift in the UV-vis absorption spectra in comparison with the methine-benzenoidal constitutional isomers (by 61 nm in dioxane). Herein, using comprehensive quantum chemical calculations with various functionals and solvent formalisms in 10 solvents with different polarities, we demonstrated that the formation of the quinoidal moiety plays a decisive role in this redshift. We further showed that the inclusion of a quinoidal unit without increasing the molecular size represents a general design strategy for the bathochromic shifts of many organic dyes.