Consumer demand for foods and cosmetics containing naturally derived ingredients has been increasing. Naturally derived anthocyanins (ACNs), from fruits and vegetables, were previously demonstrated to provide a wide range of hues as lipstick colorants with high stability. Therefore, the objective of this study was to evaluate the use of ACNs as bioactive pigments in lipstick formulations. Commercially available sources of nonacylated and acylated derivatives of the six major ACN aglycones were incorporated into a commercial lipstick base. The ACN-containing lipsticks were evaluated for their ability to act as ultraviolet (UV) absorbers [a source of sun protection factor (SPF)], free radical scavengers against 2,2-diphenyl-1-picrylhydrazyl (DPPH), and preventers of melanin formation through tyrosinase inhibition. All formulas showed increased UV absorption over the lipstick base, and acylated ACNs contributed to the highest in vitro SPF (UVB) values (≥15.8) in formulations. All formulas exhibited high inhibition of DPPH free radicals and inhibition of melanin production by tyrosinase at microgram per milligram concentrations similar to or less than kojic acid (2.41 ± 0.06 µg/mg). This is physiologically relevant because lipstick use is on average 24 mg/day. This study suggests the potential for ACNs to be used as biologically active ingredients in lipstick formulations by acting as antioxidants and UV-protection and antiaging compounds.