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Chicago Inspired Street Fashion

Chicago Inspired Street Fashion

Headed to the windy city? Here’s your men’s must-have style guide to dressing accordingly  when visiting Chi-town!

Styles are heavily influenced by climate wherever you go. The one interesting thing about Chicago, however, is that the locals dress to impress in spite of the weather. Chi-town's temperatures can plummet to a low of 22 degrees (F) in the winter and rise to a high of 90 degrees in the summer. Though Chicago ranks number 12 of the windiest cities in the U.S., it didn’t get its nickname for nothing. Chi-town is notorious for colder temperatures so be sure to prepare for your visit right!

Dressing for Chicago: Men’s Street Style Tips

If you’re visiting Chicago in the winter, that means layers on layers only. Here are a few layer options to prepare for chilly Chi-town days:

  • Puffer jackets:
  • Denim jackets:
  • Hoodies & crewnecks: 
  • Unstructured jackets:

If you’re visiting the Windy City during warmer months, lightweight and flexible will do just fine. Summer is the only time Chicago is perfect for little to no layers as sunny days can heat up to a high of 80 degrees. Men’s style for a summer in Chicago is perfect for:

  • Tees:
  • Cuban collar shirts:
  • Denim jeans:
  • Short sets:
  • Loungewear:

Chi-Town Designing: Fashion Set Apart By Details

Another important aspect of street-style for men in Chicago is the attention to detail, premium fabrics and vibrant colors and graphics. Chicago is notorious for streetwear shopping from West Loop, to Hyde Park, Logan Square and beyond. You can even find Drake’s OVO store – October’s Very Own – just off the well-known Magnificent Mile shopping row. Every store is chocked-full of custom graphic styles and designs. Here are some style details to look for when shopping like a true Chi-city trend-setter:

  • Paint splatter
  • Embellishments
  • Deconstructed details
  • Premium fabric
  • Two-tone construction
  • Chenille patches
  • Custom embroidery 

Chicago Streetwear Brands

Add Rockstar Original to the list of mens streetwear brands inspired by Chicago. No matter if you’re taking a trip down to Chicago or you’re trying to match the Chi-City energy all around the world, check out the latest arrivals at Rockstar Original to get on trend with Chicago-approved swag!