Possible Clues:

• Type of builder on the board of monopoly keeps a cool head out west
• Old West headgear
• Headgear (for ranchers?)
• Do not change it boy - it's what John Wayne wore!
• Accessory often worn with boots
• It may be felt in Westerns
• Headwear seen at a rodeo
• Line dancer's topper
• Old West symbol
• Type of builder on the board of monopoly is one of those targeted by Indians perhaps