How to Survive a Chicago Winter

Chicago lifestyle blogger Jessica Sturdy wearing a Canada Goose jacket with a Polene top handle bag.

Who else is ready to say peace the eff out to winter?! While it hasn’t snowed in a few weeks, it was well under freezing all friggen weekend here in Chicago. Since moving to Chicago, one of the main questions I get asked is, “How do you survive the winter?!” This post isn’t specific to Chicago, but here are my best tips for trying to stay warm all winter long. (Even if winter lasts well into April… 🙄)

Jessica Sturdy shares tips for surviving winter in Chicago, wearing a pom beanie, Canada Goose coat, fur booties, and a Polene top handle bag.

Let me start off by saying… As with most things in life, I think it’s mostly a mental game. Around the holidays is usually fine because there is a lot of excitement and winter is still relatively new, but January is when shit starts to get rough. February is even worse, and March (or April) is when we’re all at the end of our ropes.

This winter hasn’t been as bad as bad as last year (in my opinion) because it’s at least been pretty sunny. Last winter was a real doozy! Don’t quote me on the specifics, but I think out of like 30 days, the sun only shined for like 3 of them last year. The constant grey haze affects my energy, mood, and, and sprit so much!

My biggest tip is to try your hardest to plan a sunny getaway sometime between January – March. Even if it’s just a weekend away visiting grandparents, put your credit card miles to good use. A few short days in the sunshine does wonders for the soul!

But for when you’re not on vacation and stuck in a winter wonderland, here are five things that help me get by…

Jessica Sturdy wearing a fur-trimmed, hooded Canada Goose jacket with a pom beanie.

Jessica Sturdy wearing a fur-trimmed, hooded Canada Goose jacket with a pom beanie, matte aviators, and a Polene top handle bag.

1. Canada Goose Coat

Guys, a Canada Goose such an investment, but it’s truly a must in my eyes. I saved up and finally bought one last winter and I was kicking myself for waiting so long once I finally got it. (I have the black Shelburne Parka.) I really does make SUCH a huge difference! I used to turn my nose up at the thought of wearing a puffy coat, but those days are long behind us. It’s the warmest thing I’ve ever worn and has done wonders for my mental sanity in the winter!

They’re hard to track down this time of year (your best bet is to buy one in the fall before they sell out so you’ve got your pick of sizes and colors!), but Neiman Marcus seems to have the best selection of colors and sizes right now.

Jessica Sturdy wearing a fur-trimmed, hooded Canada Goose jacket with a pom beanie, matte aviators, booties, and a Polene top handle bag by Lake Michigan.

2. Beanies, Beanies, & more Beanies

Beanies are by no means for aesthetic purposes at this point. They really do keep you that much warmer! I don’t leave my house without a warm hat unless it’s over 45 degrees. Period. I’ve got a whole collection at this point — cuter styles and ones that are more casual/sporty for running errands or going to-and-from workouts.

I will say, you do have to be careful with letting your skin breathe though. I have a bad habit of wearing them when I’m in my apartment, too, and I’ve noticed that the skin on my forehead can get kind of irritated. So try to stick to outdoors only!

And a little side note on the workout front: I absolutely *always* wash my face before putting a beanie on my sweaty skin. That’s just asking for breakouts.

Jessica Sturdy wearing a fur-trimmed, hooded Canada Goose jacket with a pom beanie, matte aviators, booties, and a Polene top handle bag.

3. Turtlenecks Always

I joke that Steve Jobs is my style icon, but turtlenecks are like my security blanket in the winter. (My friends give me so much shit that I’m constantly in a turtleneck… Like, even out at a club on a Saturday night. 😂) They really do keep me so much warmer than a regular top or sweater, and since I’m such a baby about being cold, I’ll deal with them poking fun and my own man-repelling ways.

Jessica Sturdy wearing fur-trimmed booties with black denim for winter in Chicago.

4. Boots with the Fur

Fleece, fur, or shearling-lined booties are a must. My feet are always cold so thick socks and warm boots are a non-negotiable.

These boots are a few years old from M.Gemi, but I’ve also collected a few pairs of Sorels over the years for when it’s snowy.

Check out this post for another pair of my more casual shearling-lined booties!

Jessica Sturdy shares tips for surviving cold winters in Chicago, wearing a Canada Goose coat.

5. Tech-Friendly Gloves

I have the cashmere version of this pair and I swear by them! Not having to rip your glove off to answer the phone or a text is a game-changer.

Jessica Sturdy wearing a fur-trimmed, hooded Canada Goose jacket with a pom beanie and matte aviators.

Jessica Sturdy wearing a fur-trimmed, hooded Canada Goose jacket with a pom beanie, matte aviators, booties, and a Polene top handle bag.

Get the Look…

Canada Goose Shelburne Parka
525 America Turtleneck
Rag & Bone Jeans
M.Gemi Fur-Lined Wedge Booties (similar here)
Yves Salomon Pom Beanie (on sale here!)
Le Specs Black Aviator Sunglasses (also available here!)
Echo Cashmere Tech-Friendly Gloves
Polene Paris Top-Handle Bag

Chicago blogger Jessica Sturdy reviews a Canada Goose coat for winter.

Jessica Sturdy wearing a fur-trimmed, hooded Canada Goose jacket with a pom beanie and matte aviators.

Jessica Sturdy wearing a fur-trimmed, hooded Canada Goose jacket with a pom beanie, matte aviators, booties, and a Polene top handle bag by Lake Michigan.

Since winter is (hopefully!) on it’s way out, I made this graphic so you can pin this post for next winter!

Jessica Sturdy shares her five favorite cold-weather pieces and tips for surviving a Chicago winter.

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9 Comments

  1. 4.2.18
    Kendal commented:

    I couldn’t agree more with these tips! I’m getting through my first Boston winter right now and it is definitely a mental game! My Canada Goose coat has been an absolute lifesaver, too! Here’s to warm weather soon!

    Kendal / Life With Kendal

  2. 4.2.18
    Merritt Beck commented:

    You look so cute bundled up in that big coat! I’m loving your sunglasses and beanie too!!

    xx, Merritt
    The Style Scribe

  3. 4.2.18
    Allie commented:

    When I lived in Boston turtlenecks where my staple too! I recently heard the saying there’s no such thing as bad weather only bad clothing and it’s become a life mantra of mine! Wishing you sunshine, xAllie http://www.theallthatglittersblog.com

  4. 4.2.18
    R commented:

    I’m moving to Chicago this summer, so I NEEDED THIS POST. I’m not ready for the artic temps!

  5. 4.3.18
    Rena commented:

    I see you prefer similar clothes as I do during our winter in Bavaria 🙂
    xx from Bavaria/Germany, Rena
    http://www.dressedwithsoul.com

  6. 4.7.18
    Emily commented:

    this outfit is so cute! xo

    https://www.dearserendipity.com/