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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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When it comes to perfect Valentine’s Day gifts, there’s almost nothing that competes with the collaborative cocktail kits released in partnership between Oak & Eden and Cheeky Cocktails. Available in Espresso and Napa options, each kit combines a unique Oak & Eden spirit, Cheeky syrup and a rocks glass that will take any holiday to the next level–whether you’re celebrating solo or with your special someone. As if all that wasn’t enough, you even get 10% off with code COOLWHISKEY at checkout (thru the end of February), so you have no reason not to pick yourself up some as well when you get your Oak & Eden Cocktail Kits today.