I would split it at the seam on the top and instead of adding elastic to it, I'd use another long piece. I think the chance of it coming apart will be a lot greater if there's a couple cuts and reattachments. Have you ever put elastic in pants before? If not, the easiest thing to do it get a large safety pin, attach it to one end and run it through using the safety pin. It's a lot easier to maneuver through the fabric. Cut the elastic about an inch bigger than his waist, run it through, make sure it's not twisted, overlap the inch, sew a couple of times to reinforce and close the seam.
ETA: I just reread your post and is there no elastic in it to begin with? You want to just add some?