An Amusing Song About One Man’s Desire to Wear Hats

Comedian Brian David Gilbert sang an amusing song about his desire to effortlessly wear hats without looking like he’s trying to be something that he’s not. He cites a number of things he’d like to not look like while wearing a cap but has trouble seeing himself as he truly is.

I wish that I could wear hats Without looking like a little lad Or looking like a little league dad Or looking like a guy named Chad But it seems my head will have to stay without a bowler or beret Lest someone sees me and they say “Is that his style or bad cosplay?”

The song also reveals the singer’s insecurity around what others think of him and how they can pull of anything without any apparent effort.

And how can I look how I look and not care? Comparing my clothes with others, much closer to their own goals or some sort of closure, How do they do what they want and look planned?

Lori Dorn
Lori Dorn

Lori is a Laughing Squid Contributing Editor based in New York City who has been writing blog posts for over a decade. She also enjoys making jewelry, playing guitar, taking photos and mixing craft cocktails.