Stetson’s iconic “Boss of the Plains” hat, to the straw cowboy hats with their wide brims perfect for keeping cool in the hotter months, there’s a hat style for every cowboy or cowgirl.

Stetson cowboy hats are an iconic American accessory. The popular Skyline style will cost you $245, while other premium varieties can set you back $5,000. Over the years, famous figures like ...