Anthocyanins are often acylated with trans-hydroxycinnamic acids but can undergo a structural transformation to their cis-isomer. This study investigated the reversible photochromism of trans- and cis-acylated delphinidin derivatives (Dp) under industry-accessible ultraviolet (UV) and visible energies and their impact on color expression. Delphinidin-3-(trans-p-coumaroyl)-rutinoside-5-glucoside, delphinidin-3-(cis-p-coumaroyl)-rutinoside-5-glucoside, and its mixture were subjected to UV and visible light for up to 20 h. Isomerization was monitored by high-performance liquid chromatography with a photodiode array (HPLC-PDA). Color, spectra, and stability were compared using a spectrophotometer and ColorBySpectra software. All light treatments induced photoisomerization between trans- and cis-acylated Dp, but to varying extents and equilibria and at different exposure times. Visible energy induced greater trans-to-cis isomerization, while UV induced greater cis-to-trans isomerization. Cis-Dp showed greater color intensity and stability at pH 1 and a greener hue (h*ab 130°) than trans-Dp (h*ab 188°) at pH 8 after equilibration for 15 min.