Fat guys and old men took over newsboy hats once newsboys had to start wearing helmets while delivering the morning paper.
Maybe it's okay if you rid a plane of snakes
That was in 1974 and now that we’re almost in the future many people have newsboy hats in the wardrobe – some people have a few. And why not? They are easy to maintain, are great for going out on Friday night or leisurely walking your dog while trying not to look creepy at the park on a Sunday afternoon.
However there are a few unspoken rules to the newboy hat.
Rule One: Many styles allow the bill to unbutton from the front material, causing it will poof upward which is okay as long as you are comfortable telling child after child that – no – you are not a train conductor.
Rule Two: And this is the important rule – never wear it backwards. It gives a look that is unnaturally aerodynamic for cloth and bill. Please don’t do it.
I went to college with a great Canadian guy named Rob who wore a newsboy hat with a Canadian leaf embroidered in the center of the back part of the hat. If he wore the hat it was on backwards and that leaf would stare out at people like a third eye about to shoot a laser beam of hockey rage and maple syrup. Everyone loved Rob, “He’s such a nice guy.” But the hat was talked about in whispers like it was a rash on the back of his neck, “Does he know….?”
I ran into Rob at a wedding a couple years ago and when the conversation reached a pause I asked if he still wore his Canadian Kangol. A longer pause followed and he said, “Yeah, sometimes. Why?”
“Do you still wear it backwards?” I asked while my wife who went to college with us decidedly walked away from the conversation.
“Yeah why?” He asked again.
“Just wondering.”
Last I heard, Rob was deported.