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Vintage Chicago Hats

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Our Vintage Chicago Hats sold out quickly! Explore similar styles now!

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  • MENS - Gratitude Chicago Retro Trucker Hat - Black/Blue

    Gratitude Chicago Retro Trucker Hat

    Men's Black/Blue
    25% off
    Sale
  • MENS - New Era White Sox 5950 '05 WS Cap - White/Black

    New Era White Sox 5950 '05 WS Cap

    Men's White/Black     $45
  • MENS - New Era White Sox 59FIFTY 95 Years Cap - Blue/White

    New Era White Sox 59FIFTY 95 Years Cap

    Men's Blue/White
    29% off
    Sale
  • MENS - New Era White Sox 950AF Curve '05 World Series Cap - Carolina

    New Era White Sox 950AF Curve '05 World Series Cap

    Men's Carolina     $35
  • MENS - New Era MLB 2005 World Series Patch Fitted Cap - Black/White

    New Era MLB 2005 World Series Patch Fitted Cap

    Men's Black/White
    38% off
    Sale
  • MENS - New Era White Sox 950 A Frame 2003 ASG Curve Cap - Wheat/Cord

    New Era White Sox 950 A Frame 2003 ASG Curve Cap

    Men's Wheat/Cord
    43% off
    Sale
  • MENS - New Era MLB 2016 World Series Patch Fitted Cap - Royal/White

    New Era MLB 2016 World Series Patch Fitted Cap

    Men's Royal/White     $48
  • ADULT - New Era White Sox 9Fifty 05 World Series - Black/Silver

    New Era White Sox 9Fifty 05 World Series

    Adult Black/Silver
    14% off
    Sale

You May Also Like

  • - New Era White Sox 59FIFTY 05 World Series Cap - Green/Tan

    New Era White Sox 59FIFTY 05 World Series Cap

    Green/Tan
    29% off
    Sale
  • - New Era White Sox 5950 Fitted Hat - Light Royal/White

    New Era White Sox 5950 Fitted Hat

    Light Royal/White
    29% off
    Sale
  • - New Era White Sox 59Fifty Authentic Cap - Multi/Navy

    New Era White Sox 59Fifty Authentic Cap

    Multi/Navy     $50
  • - New Era White Sox 9Fifty A-Frame Curve '05 WS Cap - Navy/White

    New Era White Sox 9Fifty A-Frame Curve '05 WS Cap

    Navy/White     $35
  • - New Era White Sox 59Fifty City Connect Fitted Cap - Multi

    New Era White Sox 59Fifty City Connect Fitted Cap

    Multi     $46
  • - New Era White Sox Evergreen Trucker Hat - Black/White

    New Era White Sox Evergreen Trucker Hat

    Black/White     $37
  • - New Era White Sox 9Fifty AF Curve 95th Cap - Multi/Tan

    New Era White Sox 9Fifty AF Curve 95th Cap

    Multi/Tan     $35
  • - New Era White Sox 59Fifty 95th Cap - Blue/Multi

    New Era White Sox 59Fifty 95th Cap

    Blue/Multi     $45
  • - New Era White Sox 950AF Curve 95th Anniversary Cap - Gray/Black

    New Era White Sox 950AF Curve 95th Anniversary Cap

    Gray/Black     $35
  • - New Era White Sox 950AF Curve 50th Anniversary Cap - Black/Gold

    New Era White Sox 950AF Curve 50th Anniversary Cap

    Black/Gold
    14% off
    Sale
  • - New Era White Sox 59Fifty Felt Fitted Cap - Black

    New Era White Sox 59Fifty Felt Fitted Cap

    Black     $50
  • - New Era White Sox 950 WS Cap - Brown/Blue

    New Era White Sox 950 WS Cap

    Brown/Blue
    14% off
    Sale
  • - New Era Yankees 59FIFTY 96 World Series Cap - White/Blue

    New Era Yankees 59FIFTY 96 World Series Cap

    White/Blue
    29% off
    Sale
  • - New Era Yankees 950 A Frame 2000 World Series Curve Cap - Wheat/Cord

    New Era Yankees 950 A Frame 2000 World Series Curve Cap

    Wheat/Cord
    43% off
    Sale
  • - New Era White Sox 5950 Cap - Brown

    New Era White Sox 5950 Cap

    Brown
    17% off
    Sale
  • - New Era White Sox 940M Crown A Frame Cap - Black

    New Era White Sox 940M Crown A Frame Cap

    Black     $33

About Vintage Chicago Hats


Step back in time and showcase your love for the Windy City with our collection of vintage Chicago hats. Each piece is designed to capture the essence of Chicago's rich sports history, featuring classic styles that never go out of fashion. Whether you're looking for a fitted cap or a relaxed trucker style, these hats are perfect for any occasion.

Crafted with quality materials, our vintage hats offer comfort and durability while making a bold statement. With unique designs and nostalgic elements, they are ideal for fans and collectors alike. Elevate your wardrobe and celebrate Chicago's iconic sports culture with these timeless accessories that blend style and heritage seamlessly.