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Preparing For The Chicago Tundra

Cat Strain ponders Chicago’s winter survival requirements.

By F+, Featured

Illustration by RIN

Everyone who has moved to Chicago has been accosted by a Chi-native about their winter weather:


“Do you have the right clothing?”

“The winter is brutal.”

“Do you have HeatTech underclothes?”

“Make sure you have the right shoes.”

“Yeah, you say you’re prepared, but just wait until you experience that wind chill.”


We immigrants from warmer, even tepid climates believe our North Face windbreakers and Dr. Martens are enough to tramp through the city streets, but oh, do we discover the extent of our insolence.


Chicago winters are dark, damp, and delightful, despite the skin-ripping chill of below-zero winds and tramping through the brown slush to get to the CTA. It’s only in this darker season that everything freezes — quite literally — and the city becomes just slow enough to borrow time in the glory that is the frozen Lake Michigan and Chicago River. Rather than grumping about the below-zero temperatures, relish the opportunity to admire the famous snow-dusted architecture that makes this city the Third Coast.


As with any outdoor excursion, you need the right gear:

  • Compression Socks: These suckers help to prevent swelling and keep your pants in place. Let no crack in your clothing be present. Beware the wrath of wind-chill.
  • Wool Pants: Embrace your inner 1920s newsboy and slip into the toasty joy of wool. Do yourself a favor and hit the nearest thrift shop for some old-school, fabric-lined wool trousers. Your nether-bits, buttocks, and legs will thank you.
  • HeatTech fabric: Holy cow is this stuff a lifesaver. Picture this: You enter Uniqlo, pick up a cellophane-wrapped long-sleeve shirt, “how in the world will this weird, silky, six-dollar shirt help me?” Oh, it will. Think of the HeatTech like a slip, the kind worn under dresses and skirts. The slippery fabric ensures that your clothing doesn’t stick or wrinkle in odd places and keeps body-heat trapped in close.
  • Beanie: You release the most heat through your head and appendages. Wear a damn hat.
  • Gloves: Your coffee is not warm enough to prevent frostbite. Buy some gloves, wear them, thank me later.
  • Scarf: the ultimate to-go blanket and fashion accessory.
  • Waterproof Winter Boots: The worst feeling in the world is stepping into a wet spot with socks on. Now imagine that’s your entire foot, like, all day.


  • Heated Pod: The latest invention from Tesla and Lyft. For a mere kabillion Bitcoin, you can own a personal barge to transport you to school. It comes in Space Gray and Money Moss Green.
  • Sleeping-bag Jumper: Ignore all previous advice and cut holes in the bottom of a sleeping bag for your feet. Pro-tip: Purchase a “mummy” version so your winter cocoon can be re-stuffed into its sheath and fit in your bag while inside.


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