Overall, the straw hat season is influenced by a combination of climate and weather patterns, geographic location, and cultural and fashion trends. These work together to create a demand for straw hats during specific times of the year.. Traditionally, straw cowboy hat season runs from Memorial Day to Labor Day, while felt cowboy hats take over for the cooler months. Labor Day—the first Monday in September—marks the crossover, and by September 15th, felt season is officially here. This day celebrates both the change in weather and the classic cowboy style that comes with it.
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Felt hat season runs until May (or Memorial Day, if you want a specific date). Can You Wear Straw Hats in the Winter? Since straw hats are more informal, they are appropriate to wear every day. The only downside to wearing a straw hat in the winter is that your head gets cold quicker, and the rain seeps through. When to Wear Leather Cowboy Hats. The Season is a Changing: From Straw to Felt. When Should you Switch? The Great Switch: From Straw to Felt Every cowboy knows the feeling. One day you're brushing the dust off a straw hat that's seen every jackpot, trail ride, and late-summer event. The next, that first cool breeze rolls in, and suddenly the straw just doesn't cut it anymore. That's when it happens. The switch to felt.