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City of Chicago

City of Chicago

Wear the heart of the city on your sleeve with our official City of Chicago collection. Whether you’re a lifelong local or a visitor with love for the 312, this line captures the grit, pride, and timeless style of the Windy City. From flag-inspired designs to iconic skyline prints, shop gear that celebrates Chicago’s unique identity.

Apparel inspired by the Chicago city flag and skyline

Chicago-themed hoodies, hats, and t-shirts

Great for locals, tourists, and proud Chicagoans everywhere

Designed with Chi-Town pride

Show your love for the city that works - Chicago born, Chicago proud.

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Chicago Soft As A Grape Ladies Mauvelous Mock Neck

A black washed baseball cap shown from the back, featuring a white embroidered square patch with a monogram and the text 'ROBIN RUTH' on the crown, and 'CHICAGO' embroidered in white on the back strap. A black distressed baseball cap featuring 'CHICAGO Original' embroidered on the front. The 'CHICAGO' text is filled with a distressed, multi-colored pattern of red, pink, and white, while 'Original' is embroidered in white below it.

Chicago Black Floral Cap

White baseball cap shown from the back, featuring a square patch with the Robin Ruth logo and 'CHICAGO' embroidered on the strap. A white distressed baseball cap featuring 'CHICAGO' embroidered in colorful floral-patterned letters and 'Original' in gold below it, shown against a plain white background.

Chicago White Floral Hat

A dark heather gray short-sleeve t-shirt with a circular graphic on the chest featuring the text 'CHICAGO ILLINOIS' and 'The Windy City' in white, with a light purple accent ring.

Chicago Ladies Delphine Relaxed Fit Shirt

A light heather gray short-sleeve t-shirt with a vintage-style black graphic on the front featuring a Chicago skyline, a hot dog, and the text 'CHICAGO ILLINOIS', 'SINCE 1867', and 'The Windy City'.

Chicago Ladies Morocco Oversized Shirt

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An oversized sage green hoodie shown from the back, featuring a relaxed fit, ribbed cuffs, and a ribbed hem, photographed against a solid white background. An olive green cropped hoodie with a white graphic print on the front that reads 'THE WINDY CITY CHICAGO ILLINOIS' with a sunburst and skyline design.

Chicago Ladies Juno Soft Hoodie

A plain beige pullover hoodie shown from the back, photographed against a clean white background. A beige zip-up hoodie with a white graphic print on the left chest featuring the text 'CHICAGO' and 'Midway City' with a castle illustration, shown against a plain white background.

Chicago Ladies Milan Full Zip Hoodie

A light pink baseball cap with 'CHICAGO' embroidered in gray varsity letters outlined in white on the front, shown on a plain white background. A light pink baseball cap featuring 'CHICAGO' embroidered in varsity-style block letters with a gray outline on the front panel, set against a plain white background.

Chicago Bold Double Stitch Cap

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Chicago Glitter Flag Trucker Hat (D) - Grey

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Chicago Glitter Flag Trucker Hat (D) - Royal

Chicago Soft As A Grape Ladies Nantucket Fleece Hoody

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Chicago Soft As A Grape Ladies Snuggly Fleece Wide Rib Hoody (D)

Chicago Ladies Lower Case Embroidery Sweatshirt - Marina Teal

Chicago Ladies Lower Case Embroidery Sweatshirt - Mocha

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Chicago Ladies Kickback Boxy Shirt

Chicago Ladies Presque French Terry Hoodie

Chicago Ladies Comeback Arch Corded Crew

Chicago Ladies Hoodie with Skyline

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