With the 5" shorts, you're going with the really old school Dad stuff. Nowadays, cool dads wear cargo shorts and justify them because the extra pockets are practical (they really are!). For sure, you need a golf-themed baseball cap.
One of the high school kids last year wore relaxed-fit, faded jeans, oversized, gray sweatshirt, golf hat, white New Balances, cheater glasses and had a Baby Bjorn carrier. He also added a little paunch (sp?) to his belly. It took me a little while to figure out what he was and that he was basically making fun of me and my peer group.