In 1865, John Batterson Stetson created the first cowboy hat. His design’s wide brim shaded the neck and eyes, and when turned upside down, the crown could hold water for a horse or rider, says antiques appraiser Helaine Fendelman. This model, with its original box, dates to the 1960s. Despite a few small stains, the famed Stetson name brings a handsome estimate.
What it’s worth: $175
