What to Wear in Chicago during the Fall

Here’s everything you need to know about Chicago weather and fashion during the month of October.


October is when it starts to get chilly in Chicago – especially at night – and it’s mainly the wind that makes it so cold.

Staple Outfits

During the day:

  • Skirt with stockings or jeans
  • Booties or tennis shoes
  • Long sleeve shirt (turtlenecks are better)
  • Pea coat or jean jacket

During the night:

  • Jeans
  • Sweater or turtleneck
  • Scarf (if not wearing a turtleneck)
  • Boots or tennis shoes
  • A pea coat
This red pea coat is from Express

Published by Seizing Sunny Days

Hi, I’m Mak! I’m obsessed with affordable luxury vacations, food, style, and fitness.

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