Vintage Chicago Hats

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

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  • MENS - New Era Cubs Vintage Landscape Cap - Brown/White

    New Era Cubs Vintage Landscape Cap

    Brown/White     $34
  • MENS - New Era Cubs Vintage Landscape Cap - White/Blue

    New Era Cubs Vintage Landscape Cap

    White/Blue     $34
  • MENS - New Era White Sox 950AF Curve '05 World Series Cap - Carolina

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

    Carolina     $35

You May Also Like

  • - New Era White Sox 59Fifty Authentic Cap - Multi/Navy

    New Era White Sox 59Fifty Authentic Cap

    Multi/Navy     $50
  • - New Era White Sox Core Classic Replica Cap - Multi Coloe

    New Era White Sox Core Classic Replica Cap

    Multi Coloe     $32
  • - New Era Yankees Retro Script Cap - White/Blue

    New Era Yankees Retro Script Cap

    White/Blue
    20% off
    Sale
  • - New Era Cubs 59Fifty Authentic Cap - Royal/Red White

    New Era Cubs 59Fifty Authentic Cap

    Royal/Red White     $50
  • - New Era Red Sox Game Cap - Navy/White

    New Era Red Sox Game Cap

    Navy/White     $32
  • - 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 Cubs 59Fifty Felt Fitted Cap - Black/White

    New Era Cubs 59Fifty Felt Fitted Cap

    Black/White     $50
  • - New Era White Sox 59Fifty 95th Cap - Blue/Multi

    New Era White Sox 59Fifty 95th Cap

    Blue/Multi     $45
  • - New Era White Sox 9FIFTY A-Frame Cap - Beige/Brown

    New Era White Sox 9FIFTY A-Frame Cap

    Beige/Brown     $35
  • - New Era White Sox Felt 9FIFTY Cap - Black/White

    New Era White Sox Felt 9FIFTY Cap

    Black/White
    35% off
    Sale
  • - New Era Red Sox Alternate Cap - Navy/White

    New Era Red Sox Alternate Cap

    Navy/White     $32
  • - 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 Player Replica 9FORTY Cap - Black/White

    New Era White Sox Player Replica 9FORTY Cap

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

    New Era MLB 59Fifty World Series Side Patch Cap

    White/Blue
    38% off
    Sale
  • - New Era Cubs Player Replica 9FORTY Cap - Blue/Red

    New Era Cubs Player Replica 9FORTY Cap

    Blue/Red     $35
  • - New Era White Sox 9FIFTY A-Frame Banner Cap - Tan/Multi

    New Era White Sox 9FIFTY A-Frame Banner Cap

    Tan/Multi     $38

About Vintage Chicago Hats


Step back in time with our collection of vintage Chicago hats, perfect for showcasing your love for the Windy City. These hats feature classic designs that capture the essence of Chicago's rich history and culture. Crafted with quality materials, they offer both comfort and style, making them ideal for everyday wear or special occasions.

Whether you're looking for a snapback, fitted cap, or beanie, our vintage Chicago hats provide a unique touch to any outfit. With a variety of colors and styles, you can easily express your personality while paying homage to this iconic city. Elevate your accessory game and celebrate your Chicago pride with these timeless pieces.