What To Wear For Winter In Chicago

It’s cold in Chicago. Arctic cold. I like that adjective, almost does it justice.

I don’t mind the cold. My mental attachment to it faded a few years ago. I like it now. Winter is my downtime, it’s a quiet time, a time for me to catch up on life and my business. I read and write and learn more and revamp tours and get things ready for spring. I like snow and cold and warm nights and warm restaurants and really? More than anything? I believe that Spring needs Winter,  without the pain and sacrifice of life on the wall, spring means nothing.

I like it when you think you’re about to freeze away forever, when you don’t think you can take it another day, your body cannot be tense with cold one more minute, it’s over, IT’S OVER….and then, that 60 degree day – it just – it means you’re going to make it. It’s hope. It’s the rainbow. If all of our days are 45 degree winter days, well, 60 doesn’t mean as much.

Anyway, another thing I’ve learned living in this city is how to best protect myself against the elements. And even though it’s a fight against the cold, it’s really a giving in.

So if you want to know how to dress for a Chicago winter, here are some ideas from not only me, but other Chicagoans on Twitter and the Facebook. Keep in mind too, this advice is meant for VERY cold weather. If it’s 32, put a hat and some gloves on. This is for 20 and below:

1. Warm coat.

I have a Patagonia coat. It weighs less than air. We had a gift certificate, this is how I’m lucky enough to own a Patagonia coat. But it changes everything. A real coat, a real good coat, will change everything for you. If you can afford this part, I highly recommend it.

2. A good hat.

I finally caved with the rest of Chicago and got one of these “trapper” hats (she looks rul pretty in her hat. I look a lot like that in mine too):

It’s really stupid warm. And if you get desperate you just connect those flaps right under your chin and it’s seriously cozy.

3. Wear your scarf around your face

This is from my twitter friend @mattmaldre. He swears by it. I tried it on the way out tonight and it was really nice. It does get a little um, moist(?) inside the scarf? I kind of had to come up out of it for some breaths and go back in it. But yes, very warm and kind of moisturizing. In fact, I have a peppermint Burts Bees lip balm and with the moisturizing scarf – it was almost like Mentholatum!

4. Layers.

I think non-cold weather people get confused by layers. Here we go:

Lower half:

First I put on the leggings, then I pull some knee-high socks up over the leggings, then TWO pairs of socks, then another pair of pants over all that. Just leggings and socks is NOT LAYERING. That’s just cold. Kay.

Top half:

A long sleeved shirt. Not just a long sleeved t-shirt, it has to be a well-fitting.  And by that I mean tight – if you’re rolls are showing, but you have length at the bottom and in the sleeves – then that’s a good layering shirt. And preferably some kind of sport shirt almost – something meant to be warm. LONG sleeves, enough to go over your wrists up into your finger area so you have extra sealant when putting on mittens.  Then a sweater or very warm, heavier piece of clothing on top. Or um, two sweaters. Or another shirt and a sweater. Or long underwear and a shirt and a sweater. Or…

5. Gloves, mittens,scarves:

The scarf is very important and needs to be wrapped well.  The scarf is put on before your coat. Start at the base of neck, lower neck and wrap up to a little above your lips (so you can come out when you need to breathe).  But also criss-cross the scarf at the hollow of the neck for better coverage.

Mittens are preferred for warmth, but urban living sometimes still requires use of fingers, if gloves, so be it. Pull the long sleeve shirt, then the sweater out through the cuffs of the coat, as far up to your fingers as you can, and then pull the glove or the mitten on over all that cloth. Then, tuck the glove or mitten into the cuff of the coat if you can. You’re a lil bug in a rug.

Other pieces of advice for braving the cold include: Bourbon! Staying inside and Chicago’s favorite answer of all: eating. What are some other hints to staying warm in this lovely city of ours? Do you have any other hints for staying braving this weather?

23 thoughts on “What To Wear For Winter In Chicago

  1. Oh absolutely, I think that’s part of it! I walk to the train and back every day, that’s about a 15 minute walk. I walk the dog, so there’s that too. I think if you don’t have a car there’s a lot more walking!

    And you know, all those walks to the igloos and such!

  2. Hey Luis!

    So it can be hard to say in December. Most likely it’s going to be somewhere around 32 degrees, which is not too bad! LAYERS. you need to bring layers. Bring a few long-sleeved shirts, then bring some heavier shirts to put over those, then a fleece, or a coat or a sweatshirt or whatever. Also, hat, gloves, boots. The more clothes you bring the better!

  3. I am a SoCal girl planning a trip to Chicago at the end of January. Is this how I should be planning to dress? I will be moving to the Chicago burbs in the summer so I don’t mind investing a little bit for a winter wardrobe. I just want to get it right.

  4. Hey Alison. Yes!? YES IS THE ANSWER. January is cold. It just is. We’re supposed to have a mild winter here, but yes. Hat that covers ears – good gloves – good boots (waterproof, Uggs ain’t gonna cut it) and then layer, layer, layer. Bring a long-sleeve shirt that sits tight on the body, some kind of long underwear, tights or leggings that will go under your regular pants, sweater and scarves are a godesend. And if you’re going to be moving here, get a GOOD coat. Not a cheap coat. Spend the $$ if you have it and get a North Face or Patagonia…

  5. This has helped so much! I’m a Texas girl going to Chicago for Christmas. The layering tip: thank you! Now what about shoes? Would any type of boot be okay? I was told because of the snow, it’d be better to invest in snow boots.

  6. Hey Alex! Definitely wear some boots that can at least handle water or snow. We’re supposed to have a very mild winter, but rain or sleet or snow for sure. A couple extra pairs of socks might not hurt either! 🙂

  7. I’m heading to Chicago in February with some friends. We are from AZ…definitely NOT used to freezing temperatures as a high. This might be a silly question, but we are of course site seeing on our visit. What do you do with all the layers when you go to a museum or something? We won’t have a car…using public trans. Bring a bag to carry it all in??

  8. KENDRA! It’s a really good question, I love it actually. So yes, you’ll find that we carry coats a lot. A lot. There’s also a mysterious vortex of even in a museum or on the train, etc., you won’t get too warm, the body adjusts I think. Really you’ll find you’re just taking your coat off, not all the layers. But I do have a Patagonia coat that I can actually ball up into a tiny little thing and put it in my backpack. But you’ll find that you’re still pretty comfortable inside, even with your layers!

  9. Thanks for the advice. It’s really helpful. We are visiting Chicago next week and seems like it’s going to be in 20s with wind chill. For winter jacket, should we be looking for water resistant one. We have some pea coats and heavy jackets and wondering if it would work. We don’t to spend too on much for winter clothing which is no use back in CA.
    What kind of shoes do you recommend and would layering gloves help?

  10. Hi Srivasta!

    So it looks like it’s going to be pretty mild here for the next few weeks, so don’t worry too much. A pea coat should be fine, but if it does happen to rain that day – SKIP THE PEA COAT. You don’t have to spend a lot of money on clothes, just bring more of them. Heh. My feeling on gloves, are that gloves are gloves – you won’t need to layer them. Just bring what you got. And shoes, any shoes that can handle a bit of wet just in case. But there’s no snow, there’s none coming, it’s not going to be much colder than it is in CA! Have fun, drink a lot, eat a lot…

  11. Hello, my fiancé and I will be visiting this week and would love to get your input on what to bring for a week trip in Chicago. We are from Texas and it is still 75 degrees and humid. I read that a lot of layering will be needed and I will accommodate to that. As far as shoes, I don’t own winter shoes as I have only athletic shoes and plan on wearing those. I looked up the forecast for that weekend and it doesn’t look pretty as rain and some snow might be present. Please advise. Thanks!

  12. Hi Cuong!

    That’s right, bring layers. I few long sleeved tshirts, sweaters if you have them, scarves, hats, gloves. The shoes might end up being an issue to be honest, if it’s a lot of rain or snow, you’re going to be sad. BUT, the thing is, you can always buy what you need – you can find cheap rain/snow shoes if it turns out you need them. Best advice? Bring nice warm socks for when your tennis shoes get wet….

  13. Thanks for all this advice. I’m heading to Great Lakes in Feb and am freaked out about not being warm enough. I too am from Cali, so our cold is a balmy day for you guys!! The gloves thing still has me confused though. My hands freeze here hiking at 30degrees, so how the heck am I going to keep them warm at -9 degrees??

  14. Carmen! The glove question is THE eternal question. I believe, down in my soul of souls, that gloves are basically useless. Even mittens. Might I suggest mittens though? They are warmer, but I believe the glove and mitten game is a RACKET. So just do the best you can…

  15. A friend and I are heading to Chicago the first week of March. What is your advice for then? We are Florida girls and not sure we’re ready…

  16. We are averaging 75-82deg here at home. Will be in Chicago for this coming weekends or a basketball game and sightseeing. Will bring layers as you’ve recommended. Are there outdoor activities/tourist spots we should avoid because of the inclement weather?

  17. Lucky for you Aye, it’s going to be pretty warm this weekend! Up into the 40s! You’ll see some of us in shorts for petes sakes, enjoying lovely meals outside! Ha. I think you’ll be great this weekend, enjoy the WHOLE city! There’s nothing we don’t do here because of the cold….

  18. Hi! We are headed to Chicago in November, and would love suggestions on what kind of coat you think would be best. I feel like there are so many options between wool, down, even what level of down, etc etc., and also what kind of warm boots for walking around you would recommend? Thank you!!

  19. Thanks for this article! Coming from the tropics (Philippines) and hope to be there this Dec for a 2 week visit. Will heed your suggestions and recommendations!

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