Purchase two gaskets that fit your pool skimmer. Pool skimmers are manufactured in standard square shapes or wide mouth rectangular designs. These can be found at pool supply retailers.
Lower the water level of your pool to below the skimmer to allow enough room to work and avoid the pool spilling from the skimmer. The water can be lowered to this level by turning the multi-port valve on the filter to the "drain" setting.
Remove the caulking from the outside of the skimmer. This can be peeled off once its lifted from the skimmer. Remove the faceplate screws from the face of the skimmer and set aside. Continue removing the remaining screws behind the faceplate that attach the skimmer to the pool.
Remove the old gaskets and throw away. Apply a small amount of adhesive cement to the new gasket to hold it against the inside of the pool wall. Apply another small amount of adhesive cement to the second gasket and and place it between the outside of the pool wall and skimmer.
Reinstall the screws that hold the skimmer in place followed by the faceplate and its screws. Apply a layer of silicone caulk around the seal of the skimmer and outside pool wall.
Fill the pool water back to the halfway to two-third's point of the skimmer's vertical height. Turn your filter multi-port valve back to the "filter" setting and restart.