I was 25 and I thought that the only thing cooler then my tuxedo T shirt was my fedora.

We all have that one time in our lives where we look back now and are so embarrassed by our clothing or appearance decisions, but at the time we thought it was the BEST idea ever. Maybe you had one haircut back in the 3rd grade that your mom thought would be cute, and then it became your identity in your school for the next ten years. Maybe you got gages in your ears because Emo music made it look so cool, and now, 20 years later, your ears make you resemble a mutant from X-Men. Or maybe you thought the Mullet was a good idea…last year.

In the 9th grade, I used different color hair gel to spike my hair every day. A different color every day, and not even the normal “brown, red, and blonde.” We’re talking green, blue, orange, and any other color. And that’s not even the worst appearance decision I ever made!

The year was 2013, and the clothing decision I confidently rocked for a year as my “comedy look” was a fedora and a, “classy” black tuxedo T shirt. Even as I typed that last sentence, I cringed a little remembering how confident I was for way to long in this look!

You might wonder, how might a reasonably intelligent twenty-five year old male, who had a college degree, think that wearing a fedora as he traveled all over the southeastern US, being seen by countless crowds of people was at all a good idea? The answer is really quite simple.

A hot girl at an open mic told me she liked the fedora, once.

And that is all it took! So ladies, please remember…With great power, comes great responsibility.

I remember the night I came to the *stunning* realization that the fedora and tux shirt had to go. A comedian who performed after me spent half his set roasting my look and how it was terrible for a comedian to wear a hat.

This was not the first time a comedian had roasted me and my fedora. In fact, in the Nashville scene I had been given the nickname “Fedora the Explora” and people often said I was “Fedorable.” The difference was, this comedian actually broke down why the hat made me less funny.

He told me, and everyone else in the room, that it was a huge distraction…because it looks ridiculous and was the worst. (His words then, and my words today) Secondly, and this was a big one, the hat hid my face to the audience which made it harder for them to see my facial reactions which is part of the jokes that we deliver. Of course the wording he used to make these points was a lot funnier and more insulting, but that’s the general gist.

So that next week, I ditched the fedora. Upon the removal of the hat, I noticed two very significant things. First, my jokes were getting way bigger reactions. Because the audience could see my whole face, they had more to work with when I was trying to make them laugh. That was a relief. I was beginning to think I just wasn’t funny, but it was just my fedora!

Secondly, and perhaps more shocking, was the amount of friends that came up to me and told me “Man, I am so glad you lost the fedora! We always thought it was a bad look, but didn’t want to tell you.”

I remember thinking, “Really!?!” They thought it was a bad look, and let me wear it as I traveled all over the country for a year, and never once thought, “I mean, someone should tell him…”

So friendly PSA….Friends Don’t Let Friends Wear Fedoras. Break the news to them today, and they will thank you tomorrow!

(Honestly, some people can pull off Fedoras well but myself and the majority of the population of Earth cannot.)

And for Comedians, here’s some free advice. Everything about your appearance on stage will either distract from or aid your material. I learned this past week straight from a booker’s mouth that when they are watching the 5 minute clips that are sent to them if they see the comedian wear sandals and/or shorts, or if the comedian is sitting down while they perform, the booker won’t finish watching the clip,, and the comedian won’t get booked at the venue. In my case, not only did the hat look stupid, it covered my face and impeded my jokes from connecting with the audience as much as they could. Try performing without that hat, or those cool sun glasses hiding your eyes, and you may find your jokes get bigger laughs!

And that’s the story about the time I wore a Fedora for an entire year of my life, that I will never get back.


Do you have an story about an embarrassing look you or someone you know tried to rock and it really didn’t work? Maybe you had a funny and weird phase you’d like to share about? Please feel free to comment below with your own fun stories and thank you for reading this blogpost!


Drew

Drew Davis is a standup comedian, comedy writer and professional speaker from Nashville TN.

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