Chicago usually has fluctuating weather, dramatic, I must say, it really could drop degrees in a matter of hours. That explains why they say if you wait 5 minutes, the weather will change. So much wind, but ironically not so much as the name “The Windy City” implies. That’s another story entirely.
So, when planning a trip to the Windy City, don’t just plan by the name. Chicago has four distinct seasons; however, depending on the length of your journey, you may be facing the heat of the Amazons, frost of the Nordic, or limitless monsoon rains. So, I’ll answer you, no matter what you pack, never forget this- layers!
Fortunately, people in Chicago have mastered the art of using crafty weather to craft endless fashion opportunities.
A Chicago essential is denim. It is the clothing staple, can be in pants, skirts, jackets, and of different colors and styles. For a more blend-in, fashion-centric look, go for skinny jeans and stretchy jeggings on knee-high boots or ankle booties. Men can opt for straight-legged jeans (I’ll prefer tapered, though), under a jacked denim shirt and chukka boots. That gives you that fulfilling aura of “denimness” and fills the gap for casual wear.
Capri pants for the summer, spring and fall seasons under a free-flowing cotton shirt and jacket and a slushy beanie gives you the breezy vibes while keeping you warm and snug, especially for evening strolls.
What Women Should Wear in Chicago – (Click to expand)
Below is a sample women’s clothing list. (All items link to Amazon.com for your convenience).
What Men Should Wear in Chicago – (Click to expand)
Below is a sample men’s clothing list. (All items link to Amazon.com for your convenience).