The Gambler style hat sports a round, oval crown like a porkpie hat and a wide brim with a small upturn. Known also as a “planter’s hat” it was seen as a wealthy landowner’s classier alternative to a typical cowboy hat. Popularly seen on Rhett Butler in Gone with the Wind, it’s a practical and classic dress hat that shows off an elegant sense of southern style. We offer some premium hats from only the best brands like Dorfman Pacific, Peter Grimm, Scala and Tommy Bahama. Gambler hats are purported to have gotten their name from riverboat gamblers who tried to copy the dress style of wealthy landowners in order to seem wealthy themselves. Regardless, they were highly popular through the 19th century with both farmers and gentlemen alike. The low crown height and small brim make it an excellent choice for those who have trouble pulling off a wide-brim “cowboy” style and it remains a popular men’s western style dress hat.