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Bailey of Hollywood - Gambler

Bailey of Hollywood - Gambler

Initially branded as the Pacific Harvest Hat Company, founder George S. Bailey realized that the rising stars in Hollywood were setting the standard for high fashion and the booming population of the West Coast needed true quality hats to finish their looks. By outfitting the likes of Bing Crosby and Gary Cooper, Bailey became the go-to brand for men's hat fashion. From that point on Bailey would be known as a designer of fashionable hats and caps.

To this day, the brand continues to make waves in the fashion industry. From fedoras to pork pies, and ivy caps to ball caps, the Bailey of Hollywood division has distinguished itself as the top source for headwear superior in both caliber and design.


It’s a safe bet that our Gambler hats will take your look to the next level! Gamblers are western-style hats with distinctive crowns and ample brims that provide the image of a cool, confident high-roller. Our selection includes hats from great brands like Bailey Western, Country Gentleman, and Pantropic. We have straw options for summer and wool for winter, so we’ve got you covered year-round.

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