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

    Black/Blue
    25% off
    Sale
  • MENS - New Era White Sox 59FIFTY 95 Years Cap - Blue/White

    New Era White Sox 59FIFTY 95 Years Cap

    Blue/White
    29% off
    Sale
  • MENS - New Era MLB 1914 59Fifty Cooperstown Cap - Blue

    New Era MLB 1914 59Fifty Cooperstown Cap

    Blue     $44
  • MENS - New Era MLB 2005 World Series Patch Fitted Cap - Black/White

    New Era MLB 2005 World Series Patch Fitted Cap

    Black/White     $48
  • 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

    Wheat/Cord     $35
  • MENS - New Era White Sox ASG 50th Anniversary Cap - Black/Red

    New Era White Sox ASG 50th Anniversary Cap

    Black/Red     $42
  • MENS - New Era MLB 2016 World Series Patch Fitted Cap - Royal/White

    New Era MLB 2016 World Series Patch Fitted Cap

    Royal/White     $48

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  • - 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 59Fifty Authentic Cap - Navy/Multi

    New Era White Sox 59Fifty Authentic Cap

    Navy/Multi     $42
  • - New Era Yankees 59FIFTY 96 World Series Cap - Blue/White

    New Era Yankees 59FIFTY 96 World Series Cap

    Blue/White
    29% off
    Sale
  • - New Era Cubs 59Fifty Authentic Cap - Royal/Red White

    New Era Cubs 59Fifty Authentic Cap

    Royal/Red White     $45
  • - New Era White Sox 950 A Frame 05 World Series Curve Cap - Federal Red/Black

    New Era White Sox 950 A Frame 05 World Series Curve Cap

    Federal Red/Black     $35
  • - New Era Cubs 59Fifty Felt Fitted Cap - Black/White

    New Era Cubs 59Fifty Felt Fitted Cap

    Black/White     $50
  • - New Era White Sox 5950 Chrome Fitted Cap - White/Gold

    New Era White Sox 5950 Chrome Fitted Cap

    White/Gold     $42
  • - New Era Cubs 59Fifty 90 ASG Cap - Blue/Multi

    New Era Cubs 59Fifty 90 ASG Cap

    Blue/Multi     $45
  • - New Era White Sox 950AF Curve 50th Anniversary Cap - Black/Gold

    New Era White Sox 950AF Curve 50th Anniversary Cap

    Black/Gold     $35
  • - New Era MLB 59Fifty World Series Side Patch Cap - Blue/White

    New Era MLB 59Fifty World Series Side Patch Cap

    Blue/White
    38% off
    Sale
  • - New Era White Sox 5950 Fitted Hat - Dark Green/White

    New Era White Sox 5950 Fitted Hat

    Dark Green/White
    29% off
    Sale
  • - New Era Red Sox 59Fifty Authentic Cap - Navy/Red

    New Era Red Sox 59Fifty Authentic Cap

    Navy/Red
    33% off
    Sale
  • - New Era White Sox Felt 9FIFTY Cap - Black/White

    New Era White Sox Felt 9FIFTY Cap

    Black/White
    35% off
    Sale
  • - 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 Yankees 9Fifty A Frame World Series Cap - Navy/White

    New Era Yankees 9Fifty A Frame World Series Cap

    Navy/White     $35
  • - New Era White Sox 9Fifty AF Curve 95th Cap - Multi/Tan

    New Era White Sox 9Fifty AF Curve 95th Cap

    Multi/Tan     $35

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.