[rotorwrench]

Henry wore hats that fit the times he lived in and the weather likely played a part as well.

The Boater and Bowler hats would have been in the time that they were popular. He wore the boater when he was out at the farm in the summer months. The bowler was likely worn in cooler months of the year. Those types sort of gave way to the Fedora and Homburg types in the later years of his life.