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I have several traditional felt cowboy hats that I wear. My usual color is silverbelly (beige/light wheat), but I also have them in brown and black. Always worn with cowboy boots, and usually Wrangler jeans, but sometimes I wear a cowboy hat with a suit.
Usual etiquette for men is to wear felt hats after Labor Day, or when the weather is cool, and straw hats after Memorial Day, or when the weather is hot. A hat is a good idea to keep the sun off the head and neck while riding horses or just going about your daily business.
Here are some photos of me from images taken for this site that show me in various traditional felt cowboy hats.