Wearing a fedora at the fish hatchery in Lewistown. Bought this one shortly after reading editorial in Dig Boston.

My name is Charlie, and I wear a fedora.
I’ve been wearing one for two years now. Many times I think nothing of it.
On a recent trip to Boston, however, I read your anonymous grip on
fedora wearers, grouping us all together, associating us with the
hipster movement.
“Your friends are worried for you. They don’t like to hang with a
poser,” you wrote wrote in the July 30 issue. “Have you been listening
to a lot of ska music? Can you moonwalk like the King of Pop…if you
answered no to any of these questions, it’s time to hang up the hat.”
No Doubt, the Cherry-Poppin’ Daddies, Reel Big Fish, the Mighty Mighty
Bosstones, Sublime or even Smash Mouth have nothing to do with why I
wear a fedora, nor does Michael Jackson’s “Smooth Criminal” phase.
Reading this editorial didn’t offend me, though. It’s  not like I felt
it was a personal attack.
What this gripe did do for me was make me ask the question: why do I
wear a fedora?
“Does that particular item of haberdashery have nothing to do with
functionality and everything to do with ego?” you asked.
Actually, it started as a joke.
When I started writing for the Ranger-Review in Glendive, Montana in
2009, I would wear my father’s old brown fedora every once in a while.
It was a reporter prop. Perhaps once or twice I even wore it in the
field.
Then one week I wore it every day. I couldn’t tell you why. Just felt
natural. I started to like it.
The following Monday I walked into the Ranger office and the
receptionist asked me the question that officially made the fedora a
part of me: “where’s your hat?”
Ever since, few moments go by on the clock where I do not wear a fedora.
There is no ska involved in the story. There is also no association
with pop singer Jason Mraz, the unusual fashion statements coming out
of the indie rock scene or Chicago during the Roaring Twenties.
It is not, as you cynically stated, a “swag prop.”
I am not trying to look “a bit more interesting, mysterious and laid back.”
In fact, if I wanted to stop wearing the fedora, it’d be a challenge.
Upon leaving Glendive, several people told me, “Hey, don’t lose the hat.”
Of course, there is another stigma that comes with the fedora.
“Do you wear that hat because you’re losing your hair?” some have asked.
Why, yes, as a matter of fact, that plays a part.
At 28, I have lost a bit of hair.
This makes me think of a Hair Club for Men commercial I once saw.
“I used to be a hat guy,” the client says. “But now I don’t have to be.”
In all honesty, I like being a hat guy – no matter what’s underneath.
I feel quite comfortable wearing a fedora. May even get a wool one for
the winter, as the fedora is a particular kind of haberdashery I’ve
grown to love.