It's 2019. That means that society should have long ago reached the point where it was no longer hung up on gender stereotypes. People can do and wear whatever they want to long as it doesn't infringe on anybody else's freedom, and that makes a senior citizen wearing an impressive red dress absolutely fine in our book. More power to him.
What really sells it as an outfit, though, is the fact that he's a dead ringer for George Carlin. Everything about his face and his expression tells you that he's a deadly serious man who possesses the wisdom of the ages, but the dress says that he's a free spirit and doesn't take himself too seriously. In any event, he looks fabulous, and we're here for it. We bet he feels 90% cooler than all the guys in thee wearing jeans, too.