What To Wear For Winter In Chicago

What To Wear For Winter In Chicago?

As much as you can!? It’s cold in Chicago. Arctic cold. I like that adjective, almost does it justice.

Remember now, if you like winter, you can always come on my Badass Winter Tour! Or the Chicago Mix Tour, where we’re inside AND outside. Just sayin.

So, 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?

59 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!

  20. Hello Margaret!! I know it’s been a while since this post was published but I’m planning a trip to Chicago in he first week of January/2017 and I live in DC. It does get pretty cold here but I don’t think it’s anything comparable to Chicago from what I’ve heard. Neither of us have never been there and we will go sightseeing. I have never done this layering thing (I thought leggings and socks were it but inward wrong) so I’m doing my research because I’ll be packing for myself and for my husband, since he doesn’t know about the trip and I’ll blindly drive him to the airport and boom.. in Chicago we’ll be! It will be our anniversary and I hope we won’t want to kill me for taking him into a freezing temperature!

  21. Hi…. Once you’re at work do you change into regular clothes or are you stuck in those clothes all day? Specifically wondering about shoes,. No one can just wear winter boots at work?

  22. Hi Jessica! Oh my gosh that sounds like fun! I’ve always wanted to surprise someone with a trip like that! Call me when you’re here and we can go on a tour! Bring leggings and long underwear for him. Bring one warm, tight, under-shirt that goes under everything all day. Hats, gloves, boots. SCARF.

  23. Hi there, Im going to Chicago from dec 28 till jan 2. I am coming from Argentina, south America, so I will be. changing from a hot summer to a very cold winter. The experience I have in northern winters, january, was in Toronto, not sure it will be yhe same in Chicago. what would you recommend me to bring this year?

  24. Hi Margaret! I will be coming from Houston to Chicago next week for a company Christmas party. The party says Holiday attire and trying to come up with something that is festive, yet I won’t freeze trying to get to the party. Any suggestions on how to dress for a party and still stay warm?

  25. Hi Margaret! I will be coming to Chicago next week from Houston for a Company Holiday party. Holiday attire is suggested. Could you give me some suggestions on what a woman, not accustomed to the cold, might wear to a holiday party, shoes especially?

  26. Great information! One quick question. I’m heading into Chicago in a couple weeks and will be there for a quick weekend. We plan to go out to dinner a few nights and I’m concerned as to what people wear? Jeans, snow boots? Do they wear the same things that they wear during the day at night? I just don’t want to overpack!

  27. So I’m from Florida and have never seen snow in my life, which is why I’m so stoked to be going to chicago with some friends the 2nd week of January. It’s only going to be three days for me so I’m definitely not spending $$ on clothes for a weekend trip. What would you recommend for a three day winter wordrobe? Keep in mind I can’t really buy anything here to supplement because I’m from south florida and all our winter clothes are really thin. Should I just wait till I get there and go straight from the airport to shopping or will my layers upon layers of paper thin clothes be sufficient…oh also I’m going skiing & 🏂 🏂

  28. Hey Becky! Well, it does look like it’s going to be pretty cold and maybe snowy. So, you know what’s good? Heavier leggings. Then you could wear a cute pair of boots with them!?

  29. Hi Sherri! So like the one before you, maybe some heavier leggings and boots? That’s pretty common. You could always go with fleece tights (SO WARM) and some kind of warm dress or skirt? Depends on your dinner too, we’re pretty casual here especially when it’s COLD!

  30. Karen! oh my goodness. Yes, you’re going to need some clothes. Honestly? You should go to a thrift store and buy some really cheap (or even like Old Navy or something) long sleeve tshirts. A bunch. They can be rolled up and put away. You need a few sweaters, big ones. Get ’em cheap. Your layers of paper clothes will most likely NOT be sufficient.

  31. Hi Margaret!

    I’m going to Chicago on Thursday, and the weather report says the high is 6F!! AHH!!! I’m from Houston, so I think 40F is already too cold. I’m going there for a one-day interview, so I don’t want to buy clothes just for this trip. I’m thinking about wearing boots and leggings under dress pants. I’ll also wear a long sleeve button-down, blazer, and a coat. Do you think this will be enough for a dash from airport to hotel to office? I’m not sure how I can do a lot of layers but still keep it business casual.

  32. Hey April!

    Oh my gosh, you’ll be fine, especially in and out like that. Leggings under pants is going to do you so good, you’ll be fine. But make sure you really go outside at least once for awhile so you can really sense it…it’s something, then enjoy a fine hot toddy afterwards for all the hard work you did!

  33. I’m from Georgia but I’ll be visiting Chicago from December 16 – 19. I have tickets to the Bears-Packers game and the weather report says they’re expecting a high of 3 degrees that day. I have a trapper hat, scarf, gloves, a trenchcoat, thermal underwear, and rock climbing shoes (though they’re not boots). I also plan on taking a throw blanket to the game. Is this enough for watching the game outside in Soldier Field? Also, I are Chicago streets very slippery during the winter? I don’t mind cold weather but I’m not the best at walking on ice. I do have some of those things you can put on your shoes to give some traction on ice but I’ve never worn them. Do you have any pointers about watching the game in the cold and walking on icy cold Chicago streets as a pedestrian? I’d appreciate your advice.

  34. Hi Margaret! Great article! I’m traveling there next month for business. I live in AZ, I snowboard and have warm “snow clothes”, but I’m not sure what to wear for a business environment? Should I find weather proof heeled boots and a nice wool peacoat? Or just go with a rain boot and a puffer jacket plan to change when I get to the meeting place? Also how about the flight over? Do people change in the airport? Thanks! -Hannah

  35. Hi Hannah, Yes! you’re ethinking exactly right. Boots are always the answer, wool peacoat will help you for sure. I think if you’re coming for business, your coat, boots, warm pants will do you just fine. And yes! I have changed in the airport, so I’m sure that works!

  36. Hey Charles! well, well, well, you are going to be cold no matter what, no matter how many clothes and hats and blankets you have, you’re going to be cold on Sunday! It is going to be slippery too, we’re expecting more snow and cold before you get here. Actually, you’re already here aren’t you? The trick they tell us is to walk like a penguin, move with each side…

  37. Hey Margaret, So glad I found your tips. I will be visiting Chicago first weekend in January. First time to visit a Cold climate since South Texas doesn’t really have winter – plus we drive everywhere. I’m wondering if when you say gloves, do you mean leather gloves? I have a pair of waterproof boots, so should I just take them and not worry about a second pair for shoes? Will an umbrella be Ok since my coat isn’t waterproof.

  38. Hi Celia!

    Leather gloves are fine, fleece gloves, whatever you got, MITTENS are the best actually, but any kind of gloves. Waterproof boots are great, you shouldn’t need another pair. And an umbrella, that probably will not work. I would check the weather when you’re coming and see if we’re expecting snow. If we’re not, no need to worry about waterproof, really no need to worry about that anyway. I would only worry about waterproof if you were really going to be out in the weather. If you’re just popping in and out, no worries. But definitely NOT an umbrella. That will not survive.

  39. Hey MacZenzie! I think the trick to this is to keep certain things at your office if you can: Shoes, less bulky office clothes, etc. Winter is a lot of putting on and taking off… and it’s not really that sexy…

  40. Thank you for this! We have a daughter going to Wheaton and she just wants WARM pants that the wind won’t go through…any suggestions? Should she do a really warm legging and then just her pants?

  41. Hi
    I have to go to Chicago on February 21th for work, I’m from Cuba living in Florida so, I don’t have any idea how to dress for winter. Could you give me some tips? It’s really cold on February in Chicago ?. Thanks

  42. Well! I would start by following the advice in the post! Layer up, bring leggings for under your pants and mittens and a hat! Bring as many warm clothes and if you don’t have a lot, then you might need to buy at least a fleece or something!

  43. Hi. Going to Chicago this weekend for pleasure then staying the week for work. What type of shoes should I wear? Uggs or boots?

  44. Great info.
    If we are driving from hotel to work to restaurants…do we really need all that layering for mid – February?

  45. Nah, you should be okay. But, I say that and who knows right? It could be a blizzard then! But if you’re just kind of going from place to place, you shouldn’t need all the layers. 🙂

  46. Will be in Chicago beginning of March. Going to Bulls/Warriors game with corporate group. Will be doing dinner in a sky box…How to be warm, comfortable but business appropriate. Will dark jeans work somehow?

  47. Hey! If you’re going to a Bulls game, you’ll be fine, that’s all indoors! And heck, the way the weather has been going in Chicago? It’ll probably be 80 dergrees out. BUT YES, dark jeans are always fine!

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