Unworn hat a fashionable reminder of insecurities

Note: This column appears in the 6/23 issue of The Glendale Star and 6/24 issue of the Peoria Times

Months ago, while shopping at Ross, my wife convinced me to buy a hat.

I have mentioned before that I have always wanted to be a person who wears cool and hip headgear. I have always desired to wear a cowboy hat in some ironic fashion, but have yet to find one that fits well and doesn’t make me look like an idiot, nor have I found a reasonable occasion on which to potentially wear one. (I think I’ve seen too many beer commercials, as I frequently imagine myself in such a social situation, when in reality my wife and I go out approximately three times a year, and by “go out” I mean go to someone’s house and leave by 10pm.)

Anyway, this particular hat was pretty cool, especially for summer. It was the type of hat Jason Mraz would wear. Or Frank Sinatra, if he were still alive, and 20-years old, and at the beach. Plus, when I tried it on, it fit perfectly. Still, I was hesitant to buy it because I knew I would never actually wear it.

I tried to explain to my wife that I’m not a cool hat guy, and that it’s too late in life for me to become one. My buddy Rashad is a cool hat guy. He wears the type of hats that Irish gangters wear—he’s not even Irish; I’m Irish!—and it looks totally normal and stylish. Last year we all went to a festival near the beach in California and he got to stop by the cool hat stand and peruse hats. I cannot say that I was not jealous.

Well, this hat was on sale, making it impossible for my wife to leave it behind, and I was thus forced to buy it. I have not worn it.

I contemplated it, however, last weekend. We were going to a pool party at a friend’s house, and it really would have been the perfect situation to try it out. I stood in the closet and stared at the hat for a long time, ultimately deciding not to wear it. I figured that the potential coolness factor of the hat going over well did not surpass my anxiety at how the hat would be accepted, and the questions I’d have to answer. Where’d you get that hat? I didn’t know you wore hats! Do you have any other hats? Is something wrong with your head? Besides, even if people were nice to my face, I worried what would be said when we left by 10pm. I can’t believe he wore that hat! Who does he think he is, Jason Mraz?! What a dork!

I never imagined the internal crisis this hat would cause, and the insecurities it would expose. As I have said time and time again, I should have started wearing cool hats years ago. If I were a cool hat guy, all of my problems would disappear, and we’d be invited to many parties where people park their jeeps on the beach in the late evening and bring their guitars and what not.

Soon we will be visiting Rashad and his wife in L.A., which may be an even better time for me to try out the hat. Nobody knows me over there, plus you can wear a toilet seat on your head in L.A. and no one will think twice. I don't know ... I’ll think about it. I mean, I don’t want to upstage Rashad.


Prof. Brilliant said…
Maybe you should wear that tricorner hat that you begged your parents to buy you at Colonial Williamsburg.
mkenny59 said…
A young boy, innocently trying to get his Williamsburg on, and you've never let him forget it. I rue the day I begged for that tri-corner day. I rue the day.
Judy said…
I decided to start a new "hat trend" in 1975 when I bought a big, white, wide-brimmed hat (to go with my big pregnant waistline) to wear to my cousin's wedding. I was 23 and thought my friends would think it was really cool, which (they said) they did! In fact, it was such a hit that everyone wanted to wear it, but Uncle Dave won out (yes, THAT Uncle Dave)! He said he needed it to sing "Pennies From Heaven" but I never saw it after that. So, I say go for it-you're only young once! Just don't let UD see it.