Jay has been looking old off and on for about 10 years though. He has an old man face so he shouldn't be wearing hats and glasses. He looks youngest with a fresh fade and nothing covering his face. Somehow that works. Also he dresses like an old white guy with money. He doesn't dress to impress in all situations like the average person tries to do. He's rich, successful, got a nice wife, kids and the respect of generations so he doesn't have to really do anything but exist. The average person does things to prove we exist.