That is not a cowboy hat.
It’s not a bowler.....is it?
It’s not a helmet...
and baseball caps had not yet become popular...
It’s a western style hat with a wide brim,,,this one is a dress hat for courting or classy travel...
Jessie wore a friggin hat...as most every man in the west and mid west did.
As I do. If you want the rest of the picures showing him with a hat, you can look them up, but there are not many pictures of him..as he did not like having his picture taken...”steals the soul”