Coumarin and its derivatives possess interesting biological, pharmacological, biochemical, therapeutic, and photochemical properties. Previously reported studies have demonstrated the properties of coumarins in the inhibition of skin aging-related enzymes as tyrosinase, elastase and collagenase. Skin aging process depends on several intrinsic and extrinsic phenomena, and degradation of proteins of extracellular matrix represents one of the main causes of alteration of the skin integrity, as well as the appearance of hyperpigmented spots due to the tyrosinase activity. Our previous studies have proved that both simple hydroxycoumarins and hydroxy-3-arylcoumarins are interesting scaffolds to modulate the tyrosinase inhibitory activity. According to these considerations, we have modulated the 3-arylcoumarin scaffold to improve the inhibitory potency against tyrosinase, as well as elastase and collagenase. We have also selected for this study, benzo[f]coumarins, with an extra phenyl ring on the coumarin scaffold. In the present study a screening of hydroxy substituted 3-arylcoumarins and 3-arylbenzo[f]coumarins has been performed, with the aim of identifying compounds with potential inhibitory activity against key target enzymes for the prevention and treatment of skin photoaging. This preliminary study gives some insights into the synthesis and biological activity of these molecules against these important targets.