Ode to Pops

Everybody loves their dad. He is that guy who will do just about anything for his kids. Anything that is, besides changing his wardrobe.
At what point does dad go from being a hip twenty something guy to a fashion deficient source of jokes.
At what point does wearing a NASCAR shirt, replete with 26 different colors, become the epitomy of fashion?
At what point do you regress from shoes with laces to shoes with Velcro?
At what point does the thought of keeping the leisure suit forever come into his mind? At what point does the leather jacket with patches come back in style?
At what point does he feel that his pants pockets simply are not big enough and he needs to resort to a black leather fanny pack?
At what point do Wrangler jeans, that are two sizes too small, become the hip new accessory to said fanny pack?
At what point does the cell phone become a fashion accessory for your belt?
At what point does the trucker hat go from being a cool head piece for kids to the bat signal for dorky dad?
At what point do you no longer update your eyeglass style from hipster to wire and bottle cap?
At what point do Tevas and socks become cool?
One question I do know the answer to: At what point does wearing tight khaki gym teacher shorts become cool? The day you became a teenager and he was too afraid to get neutered. So instead he decided to slowly strangle his nads.