I’ve never seen anyone do this.
Not one…

Flat cap with fold-down ear warmers. It’s like a sophisticated baseball cap, and you won’t freeze your ears off when it hits -10.
Remember when silly hats the key factor in determining who should go to war with who?
Mine is a Boonie hat in digicam that I made myself from scratch

Your face camo works better with that terrain than the hat camo
My hat’s a tactical cap with hook-and-loop mounting points, where I change out various morale patches based on what I’m feeling that day. (A lot of times it’s the X-COM “vigilo confido” patch haha.)
So does the hat choose my personality? Or does my personality choose the hat? Who’s to say. It’s flexible and open to change at least. :D

Imma hillychopter
As long as it’s not the maga hat we good fam.
As a 49ers fan I carry a little extra hate for them choosing a red hat to signify their shittiness.
Same as a Chicago Bulls fan.
The wind easily blew my hat off the other day…that’s when I realized I bought it more than 15 years ago and it’s probably time to update old faithful.
I have a collection of toques for winter and keep another collection of ballcaps from various places, mostly museums and zoos. The one I got for visiting the Smithsonian was a Washington D.C. one, though, and it doesn’t cover my head well.
Damn.
I was about to make a joke about a dumb novelty hat I wore my senior year of college… then realized I wore it so much that if I did so, there’d be a non-zero chance I might accidentally dox myself lol
I’m sure they were mass produced, but Murphy’s Law is a cruel mistress haha

Haha, I’m glad I’m not like that…
remembers the blue hat I wear every day
Ah, crap.
Same exact reaction.
“At least I don’t wear a hat.”
Except for that blue cadet-style cap you got in Colorado that you liked because it, combined with your beard, made you look vaguely like a train conductor or a maybe a Union soldier and also expressed your love of mountains which you wear almost every morning when walking your dog to hide your bed-head.
“Fuck.”
I try to pull off a hat and end up like this:

How euphoric (do people still make that joke?)
Probably, I recently saw someone make that joke on social media.
I waited until 40 and went with the rave/dance festival bucket hat






