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Chicago is a city that doesn’t get its due credit. It may not have the beaches that Los Angeles boasts or the “state of mind” that New York holds, but a quick look on the streets will support the fact that Chicago holds its own in the realm of fashion. A mix of dark street-wear and utilitarian workwear, as well as high fashion and fabrics make the DNA of Chicago fashion one all its own. Ask anyone from Chicago and they’ll be quick to tell you that there is a connection that runs deeper than it simply being their hometown. The allegiance Chicago’s population has with their city is unparalleled, and these brands encapsulate that. Chicago may not be NYC, ATL or LA, but it doesn’t want to be either. Pick up something from one of the Chicago-based companies below and support the city that is second to none.

  • Iridium – Grey and White Zip Crewneck – $75
  • Makers and Riders Garments – 4 Season Modular Wool Pant – $169
  • Oak Street Boot Makers – Black Dainite Trench Boot – $462
  • Fourth is King – FIK Amigo Patch Wool Hat – Speckled Gray – $44
  • Jugrnaut Chicago – Jugrnaut PRPL Label Cut and Sew Denim Jacket – $170
  • Defy Bags – Verbockel Roll-top Backpack in Wax Canvas – $275
  • City of Win – Champion Tee “Bully” Edition – $27
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Flint & Tinder has always been one of our favorites because they make updated, high-quality American staples–without being fussy, over-designed or bearing a huge price tag. Our latest favorite? This Flannel-Lined Waxed Trucker Jacket. With classical trucker jacket styling and a flannel-lining for warmth, this Made in the USA trucker jacket is best in class. In addition to Martexin 7oz sailcloth exterior in eight different color options, you get fully-lined body / sleeves, interior media pocket, button-flap chest pocket, 2 welt hand pockets, and finishing like F & T antique metal buttons and a modern fit. Get yours today at Huckberry