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Vintage Chicago Headwears

Headwears Vintage Chicago Gifts

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Vintage Chicago

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Chicago Flag Hat
+7 styles
+46 more

Chicago Flag Hat

Trucker Hat

$19.99

$24.99

Chicago City Skyline Flag Vintage Chicago City Visor
+1 styles
+2 more

Chicago City Skyline Flag Vintage Chicago City Visor

Valucap Bio-Washed Visor

$23.99

$29.99

Vintage Chicago Flag Santa Hat
+1 styles

Vintage Chicago Flag Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

Vintage Chicago Distressed Visor
+1 styles
+2 more

Vintage Chicago Distressed Visor

Valucap Bio-Washed Visor

$23.99

$29.99

Chicago House Music Vintage Chicago Flag Visor
+1 styles
+8 more

Chicago House Music Vintage Chicago Flag Visor

Valucap Bio-Washed Visor

$23.99

$29.99

Vintage Chicago Illinois Skyline Apparel Beanie
+7 styles
+20 more

Vintage Chicago Illinois Skyline Apparel Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Illinois Vintage Flag Santa Hat
+1 styles

Chicago Illinois Vintage Flag Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

Vintage Chicago Illinois Skyline Bears Football Santa Hat
+1 styles

Vintage Chicago Illinois Skyline Bears Football Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

Vintage Chicago Flag Bucket Hat
+1 styles

Vintage Chicago Flag Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Vintage Chicago Illinois Est. 1833 Gift Visor
+1 styles
+2 more

Vintage Chicago Illinois Est. 1833 Gift Visor

Valucap Bio-Washed Visor

$23.99

$29.99

Vintage Chicago The Windy City Illinois EST 1848 Visor
+1 styles
+8 more

Vintage Chicago The Windy City Illinois EST 1848 Visor

Valucap Bio-Washed Visor

$23.99

$29.99

Cool Bear With Beanie Sunglasses Vintage Chicago Santa Hat
+1 styles

Cool Bear With Beanie Sunglasses Vintage Chicago Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

Vintage Chicago Illinois Est. 1833 Souvenir Visor
+1 styles
+2 more

Vintage Chicago Illinois Est. 1833 Souvenir Visor

Valucap Bio-Washed Visor

$23.99

$29.99

70S 80S Usa City Vintage Chicago Bucket Hat
+1 styles

70S 80S Usa City Vintage Chicago Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Us American City 70S Retro Usa Vintage Chicago Visor
+1 styles
+2 more

Us American City 70S Retro Usa Vintage Chicago Visor

Valucap Bio-Washed Visor

$23.99

$29.99

Vintage Chicago Illinois Flag Tees Skyline Bucket Hat
+1 styles
+1 more

Vintage Chicago Illinois Flag Tees Skyline Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago City Flag Distressed Bear Gift Bucket Hat
+1 styles
+1 more

Chicago City Flag Distressed Bear Gift Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago City Flag Vintage Bucket Hat
+1 styles
+1 more

Chicago City Flag Vintage Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago Flag 312 Bucket Hat
+1 styles
+1 more

Chicago Flag 312 Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Vintage Chicago Flag Beanie
+7 styles
+20 more

Vintage Chicago Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Vintage Chicago Baseball Emblem Visor
+1 styles
+8 more

Vintage Chicago Baseball Emblem Visor

Valucap Bio-Washed Visor

$23.99

$29.99

Chicago Flag Vintage Hat
+7 styles
+46 more

Chicago Flag Vintage Hat

Trucker Hat

$19.99

$24.99

Chicago Vintage Skyline Retro Illinois Pride Gift Beanie
+7 styles
+16 more

Chicago Vintage Skyline Retro Illinois Pride Gift Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Illinois Stamp Logo Santa Hat
+1 styles

Chicago Illinois Stamp Logo Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

Cahokia Illinois Vintage Logo Beanie
+7 styles
+20 more

Cahokia Illinois Vintage Logo Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Football Mack Attack 52 Santa Hat
+1 styles

Football Mack Attack 52 Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

The Original Berf Of Chicagoland Bucket Hat
+1 styles

The Original Berf Of Chicagoland Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

All That Jazz Bucket Hat
+1 styles

All That Jazz Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago Vintage 80s Retro Style Funny Gift Bucket Hat
+1 styles
+1 more

Chicago Vintage 80s Retro Style Funny Gift Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Retro Bears Girl Messy Bun Sports Fan Team Spirit Hat
+7 styles
+25 more

Retro Bears Girl Messy Bun Sports Fan Team Spirit Hat

Trucker Hat

$19.99

$24.99

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