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Bailey of Hollywood - Sperry

Bailey of Hollywood - Sperry

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.


Sperry Top-Sider is a classic American brand that was born in 1935 in New England. Founder Paul Sperry, a sailor and part-time inventor, wanted a comfortable shoe to wear on the slippery surface of his boat, so he developed the first boat shoe and introduced it to the world. Sperry Top-Sider soon became known as the ultimate fashion brand for the casual sophistication of the nautical lifestyle. That reputation persists today, and they’ve expanded beyond their iconic shoes to offer accessories like these hats and caps that we’re proud to have on hats.com!

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  • Lorant Ivy Cap

    Lorant Ivy Cap

    by Bailey of Hollywood

    See more Colors, including:
    BlackGreen
    S, M, XL, L
    $55.00
  • Butler Dockman Cap

    Butler Dockman Cap

    by Bailey of Hollywood

    See more Colors, including:
    RedBrownGreen
    S, M, XL, L
    $55.00
  • Stoke Newsboy

    Stoke Newsboy

    by Bailey of Hollywood

    See more Colors, including:
    Blue
    S, M, XL
    $55.00
  • Medd Flat Cap

    Medd Flat Cap

    by Bailey of Hollywood

    See more Colors, including:
    Plaid
    S, M, L, XL
    $55.00
  • Loring Panama Fedora

    Loring Panama Fedora

    by Bailey of Hollywood

    See more Colors, including:
    Natural
    S, M, L, XL
    $275.00
  • Inglis Fedora

    Inglis Fedora

    by Bailey of Hollywood

    See more Colors, including:
    BlackBlueGreyRed
    S, M, L, XL
    $95.00

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