Why I Was Scared to Wear Hats

“His head’s so big, he can’t wear any hats.” – Emma from Kindergarten Cop

When I was a kid, I didn’t care what people thought. I didn’t care about what I wore either. Cartoons, neon, Velcro, and anything wild from the 80’s. If it was cool to me, I’d wear it. 

Then I remember wearing hats, and my older brothers would make fun of me saying my head is so big that I make hats look abnormal. They’d also say the hat is disproportionate to my face. Punks. 

I didn’t think about wearing a hat til I started dating my wife, decades after my brothers shaming me (don’t worry all is forgiven). 

While shopping during a date, my wife comes up to me and puts a hat on my head while saying “You should wear this. It would look good on you.”

I froze. I became ten-year-old me and bashed myself with negative thoughts. 
She left the hat on my head and affirmed how “good” it looked. Since then, I’ve been confident wearing hats. 

That’s what it takes in fashion and style. Someone to breathe confidence in you, a little time to get through the discomfort and some risk to try something new. 

Is there something you’ve wanted to wear or try that you’re just not sure about? What’s something you never thought you’d wear but now wear confidently? What did it take for you to try something new?

There’s a comment section below! Let’s go!