A saddle pad assembly provides padding under a saddle while facilitating customization to inhibit undesirable pressure points from developing. The assembly includes a cover having a closed end and a perimeter wall extending from the closed end. An edge of the perimeter wall defines an open end opposite the closed end. A plurality of holes extends through the perimeter wall of the cover. The holes are arranged into a pair of opposed rows extending between the closed end and the open end. A pad is insertable into the cover through the open end. The pad has a row of apertures alignable with the rows of holes. A line may be laced through the rows and the apertures to couple the pad to the cover.