What To Wear For Winter In Chicago

January 23, 2013 12 Comments »

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?


  1. mattmaldre January 23, 2013 at 12:33 pm -

    Sometimes I like to layer fingerless gloves over stretchy gloves.

  2. Tiaras & Tantrums February 1, 2013 at 2:45 pm -

    I just want to know where the heck you are headed?? I don’t have the need to dress like that living in the burbs – I guess running from car to building has spoiled me

  3. Margaret Hicks February 3, 2013 at 4:00 pm -

    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!

  4. Roxanne February 11, 2014 at 4:42 pm -

    I’m going to Chicago for the first time in the beginning of March. Do you what the weather is like at that time? I already get cold quickly. Should I follow your guide?

  5. Margaret Hicks February 12, 2014 at 10:58 am -

    Hi Roxanne!

    My advice? Overdo it! Bring more than you think even. It’s always easier to take something off if you get too warm. Beginning of March, this year, probably still going to be pretty cold! Layers!!!! Make sure you have an undershirt or two, a warm sweater, a coat, a scarf is always helpful inside and out! I hope it’s nicer out by then, but this winter, hoo dolly…it could still be really cold!

  6. Christine February 13, 2014 at 6:47 am -

    Hi Margaret! Thanks for the tips. Im actually heading out to Chicago for a conference also in the first week of March for the first time and im quite nervous since im coming from a tropical island. Do I also need to bring rain boots or will regular knee length boots with double socks and leggings suffice? And what can I do to still enjoy the city despite the cold?

  7. Margaret Hicks February 18, 2014 at 10:14 am -

    Hi Christine! I’m going to send you an email…

  8. Monique February 23, 2014 at 5:04 pm -

    Hi! I am traveling to Chicago on Thursday from California. I am shopping for a pair of gloves that will suffice but I am not sure what will do. Any suggestions?

  9. Dana February 25, 2014 at 10:30 pm -

    I’m headed out to Chicago on tomorrow for the first time from the South and I see that the weather is brutal.

  10. Margaret Hicks February 25, 2014 at 10:38 pm -

    Dana! It is very cold here. Record breaking. LAYERS. The warmest stuff you have. You need one good undershirt, good sweater, leggins for under your pants (this is very important, makes a huge difference! Mittens, scarf, hat. You’ll be fine, we’ll show you how to do it!

  11. Margaret Hicks February 25, 2014 at 10:39 pm -

    Hi Monique! Really the answer is mittens. They’re much warmer than gloves. If you just can’t stand it, then buy some good Isotoners or whatever. My personal belief is that gloves are fairly hack. They keep your hands warm up to a point and then, the expensiveness of the glove does not matter. If you’re serious, mittens. If you can’t do it, get some nice furry, warm Isotoners…

  12. Isabella Lalla April 8, 2014 at 11:54 am -

    I’m moving to Chicago in the fall for school, and I’m from New Orleans so I’m not ready for this type of winter at all. I’d love for you to email me must needs for the winter just so im prepared.

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