A painting caddy including a housing; a strap secured to the housing in a manner to allow the housing to be secured therewith to the waist of a user; a paint reservoir vessel in connection with the housing; and at least one paint brush holder having a brush insertion vessel in connection with the housing wherein the paint reservoir vessel and the brush insertion vessel are in fluid connection through a one-way valve that allows fluid flow from the brush insertion vessel to the paint reservoir vessel and blocks fluid flow in the opposite direction.