In this area he would be a trumpster

I might lean, but I wouldn’t leap.

I might assume he has horses.......

Never....he might smell like horses steers and chewing tobacco .... Libertarians never enable Rethuglicans.... TrumpOLINI was a BILLARY demoRAT ....Chelsea & Ivanka are close Don&Hill sit in same row as Bill&Melania .....Willie Nelson sings MY HEROES HAVE ALWAYS BEEN COWBOYS .... if the hat is brand new the jerk may have just bought it for a MAGA rally .....cowboys work ...jerks wannabe rich like TrumpOLINI....ask ....they will tell you

I would assume it's a trumpist.

I have Canadian friends who own property in the US and visit often. They love their cowboy hats and are also anti Trump.
Many people in Alberta also wear them.

However, if I were in the US, perhaps unfairly, but admittedly, I may make that assumption given that the cowboy hat wearing states are typically red.

Not me.

Yes. We shouldn't generalize or sterotype, but I really enjoy it.

You can't judge someone by what kind of hat they wear. Only by what it says on the front.
If it says MAGA, he's a Trumplerite zombie (commonly known as a Zeke).
If it says Jim Beam, he's a drunk.
If it says Jesus, he's a mental patient.