Skin aging is a progressive biological process of the human body that depends, among several phenomena, on degradation of proteins of extracellular matrix as well as the appearance of hyperpigmented spots. In previous studies, we demonstrated that differently substituted 3-arylcoumarins efficiently inhibit skin aging-related enzymes, such as tyrosinase, elastase and collagenase. According to these considerations, we have modulated this scaffold to improve the inhibitory potency against tyrosinase, elastase and collagenase, extending the study to the inhibition another enzyme, hyaluronidase. Moreover, photo-protective effect of the compounds has been also evaluated by determining the Sun Protection Factor. Starting from 3-(3’-hydroxyphenyl)-6,7-dihydroxycoumarin and 3-(2’-hydroxyphenyl)-6,7-dihydroxycoumarin, that overall revealed to possess the best inhibitory effects against skin aging-related enzymes, we selected for this study new molecules including bromine atoms together with the previously studied hydroxyl groups. Some compounds present multitarget properties towards the selected enzymes, along with a good photo-protective effect. These data support our previous findings on 3-arylcoumarin as promising scaffolds for the design of skin anti-aging agents.