Knowing how to dress for Chicago winters comes down to 7 simple basics: hat, scarf, long underwear, gloves/ mittens, jacket, and 2 pairs of boots! In this post, I want to share with you my recommendations for products that I use to stay warm without the bulk. They are worth the investment, and you will use them again and again for years.
So now that we are about to begin our third winter in this fascinating city, I can share the essentials for any Chicagoan’s wardrobe between November through May. . . did I say May? . . . hahaha . . . I wish I was kidding. This post contains affiliate links, which means I receive a small commission if you decide to make a purchase if re-directed from this post at no cost to you.
Hat
When we first moved during the pandemic, my daughters and I learned to knit to kill time indoors. A couple of the easiest things to learn how to knit were scarves (more on that below) and hats/ beanies. This was actually incredibly helpful because I underestimated how important hats were to keep warm during Chicago winters. The cold wind is painful on tops of ears and sides of face. Not to mention that if someone has little to no hair, the icy air can be brutal on the skin on top of the head. I also notice that a hat keeps my long hair or bangs out of my face, especially when wind gusts kick up between buildings on Chicago streets or by the lake.
Hats are an essential; while it is debated if adults lose heat more readily through their heads than other parts of their bodies, children certainly do. But another reason to cover that head no matter how old you are is how damaging cold, dry air is to our hair and scalp! Take it from me! The dry winter months can strip our scalps of moisture and cause flaking. This is made worse by the revved up radiators and indoor heaters.
My go-to beanie is from Durio. These super comfy hats have over 2,500 reviews and rank 4.5 starts on Amazon!
What do I love about these hats?
First the stitching is superb and strong, making these hats durable for all of the twists and turns in my backpack and of course, the washer and dryer. After all, you will need a hat you can wash after an afternoon of snow shoveling!
Also, the material is as cozy as it is sturdy. The thick acrylic material is cushiony and relaxing, but still fits well and doesn’t slope or wiggle. In fact, they are so cozy, I once taught an entire 3-hour graduate course with this hat on because it felt so sweet on my head.
A major plus is how you can buy an entire set for one low price. Because you won’t need just one hat. You will need a small variety, especially if you are doing chores outside. So this is a huge bang for your buck. The Durio set comes in 4-packs! My daughters and I share about 12 of these hats all winter long.
Also, the color of the sets is so fun; I tend to dress in neutral colors, so my go-to hat choices are white, beige, cream and black, but it is great to have a hat for every occasion or when you want to add a pop of color.
Scarf
A scarf is necessary because the wind can pierce the sensitive skin around the neck on walks or on the L platforms. This is especially felt when you are wearing a coat that has an attached hoodie and there is a gap between the collar/ neckline and your face. It may not sound like much, but the cold wind takes brutal advantage of that spot.
On one hand, scarves can rev up your body temperature quite quickly, so they feel great on an extended trek from parking garage/ L platform to your destination, but you really should have two options: one for especially cold days and a lighter one for crisp days.
I love an infinity scarf for the coldest day because it hangs at just the right length to offer soft, cozy support. And the NEOSAN Womens Thick Ribbed Knit Winter Infinity Circle Loop Scarf is extra soft and thick-cut. It is basically like wearing a blanket around your neck. If you are like me, and you don’t like cold weather, this scarf makes outside conditions not just endurable, but enjoyable. I’ve been known to use this scarf as a small pillow while I was visiting Canada one spring while riding public transit- it is really that cozy!
My favorite colors are Khaki and Coffee!
My other option is the MaaMgic Womens Large Soft Cashmere Feel Pashmina Shawls Wraps Ladies Light Scarf. This scarf has such a soft, velvety smooth texture while not being overbearing like a chunky-knit blanket. This is the perfect warm option for the end of fall when the temperature is starting to dip into winter conditions because the fabric is breathable. I absolutely love the color options available, especially the earth tones and basic black. A pop of color would look great too, especially if you use this as a shawl indoors!
Long Underwear
I have one thought on this topic. I don’t like long underwear. There, I said it. Long underwear is simply a set consisting of a long-sleeve shirt and long pants that you wear under your regular clothes.
I don’t think it is necessary, but there are some people that think it is an essential here. In fact, when I moved here, friends from other comparable climates all recommended that I buy this item first. Well, without much guidance, we purchased some sets, and they were much too warm. My husband and I run pretty warm, so I’m not surprised that we overheated; however, the truth is that many buildings in Chicago have the radiators running extremely hot. If you enter a building with long underwear, it can be a tough situation. You certainly don’t want to have to go to a restroom to remove that under-layer and carry those items with you until you go home.
One reason long underwear isn’t necessary is that most people don’t spend enough time outdoors to require it. If a child walks an extended distance to school, then sure, the long underwear is necessary, but they will have to have a light set to deal with the heaters in the school building for the rest of the day.
One type of long underwear that seems reasonable is made of silk. More breathable and cool than wool, silk may be a better choice for those who have long walks to their train stop, but honestly, a quality jacket may be all you need (more on that in a bit). This option from Grenasasilk looks well worth a try.
Gloves or Mittens?
Just to be clear, mittens are warmer than gloves. Remember, mittens don’t have individual sections for each finger, and all your fingers are joined together in one pouch, sharing heat with one another. However, unless you don’t plan on using your fingers or need dexterity (think of simply going for a walk), mittens aren’t really that realistic of an option. Most of us need our fingers at the ready– to pick up dog messes, zip-up coats, grab our keys with slippery key chains, or pull out our Ventra L card to hop on that train. I haven’t been able to successfully use mittens unless I’m simply the passenger in a car.
On the coldest of days, I mostly use gloves. Some people will use gloves early in the season because of the thinner skin on their hands, and unless you’ve been in Chicago-type of cold, you may not know if your hands are sensitive as well. That is why it is a good option to have gloves or mittens ready to go because touching an ice-cold steering wheel is not fun at all.
I have the Moshi gloves above, and they are reliable and warm; however, they are not great on digital screens as advertised. If this isn’t important to you, then consider these an option! Other options I have here are from ViGrace and Trendoux. But please note, I have not yet been able to find a glove that works with digital screens, and if you have to take the glove off to use your phone, then maybe a mitten is best. A mitten usually has a mid-palm access, which means you can remove part of the mitten like the way you can with a hoodie on your head. This is convenient because you don’t have to remove the entire item, just part of it. This feature is usually called “flip top”.
The mittens I use are from Target, and are no longer available, but there are other great options currently from the same brand.
I also recently found convertible options! While I haven’t tried these Warm Wool Knit Flip Fingerless Gloves Mittens yet, I will give them a try this season. They have over 1,000 four-star ratings, so I’m eager to report if they are a smart choice.
Jacket
My favorite coat for our new climate is the Columbia’s Heavenly Long Hooded Jacket. Here’s why . . .
First, it is the perfect length. I know that there are some coats that are much longer than the one I recommend (actually, the major difference between the word “coat” and “jacket” is that a coat is a longer item of clothing). I argue that a coat is not necessary. One major reason is that a coat can be cumbersome in the city. It can be difficult to quickly sit down and get up in a crowded train, especially if your coat has a full-length zipper and not buttons. Also, if you are wearing long underwear or lined pants, then having a full-length coat isn’t really adding much to your warm layers. The real reason to have a jacket cover your bottom is to keep it warm when you encounter a brutally cold seat, like in a train or a car. Finally, a jacket this length is more manageable when you are carrying multiple items of clothing at once when you enter a heated room. Trust me, after removing and putting on a jacket multiple times, you want something lighter to carry.
Second, this jacket is light as a feather while remaining as warm as heavy coats. I mean it. When I was searching for jackets the first year I moved to Chicago, I thought that a bulkier one would be best, but that is simply not true. Jackets have come a long way, and this one has some smart technology up its sleeve (pun intended)! The jacket is lined with special “omni-heat” reflective material. When I read about this lining before I purchased it, I thought it was bunk, but it is so impressively warm without the bulk. Zipping up the jacket locks in the heat using your own body’s warmth, without the bulky layers! In addition, it is insulated with synthetic down, but just the perfect amount.
Third, despite the jacket’s warming technology, it is still breathable and comfortable. It isn’t suffocatingly hot or sweat-inducing. In fact, I am perfectly comfortable leaving this jacket on during a Target run.
A couple of extra features I adore are the fleece-lined hood and collar as well as the hand cuffs with thumb holes. These hand cuffs are essential when you forget your mittens! I think this is my favorite feature.
The jacket is very affordable when you consider the years you will get from it as well as the trusted brand-name. I’m wearing it for my third winter, and even after multiple washes each winter season, it is still as good as new.
There are a variety of beautiful colors too; I have one in Chalk and Spruce. I’m currently eyeing the blue shades as well.
Boots (Snowy Weather)
The boots I love are from L.L. Bean- the Women’s Bean Boots, 8″ Flannel-Lined, Thinsulate. These boots are so easy to wear on days when there is snow accumulated on the ground. I’ve worn them in about half a foot of snow, trudging through the yard on a non-negotiable dog walk.
I love the comfort of these boots; they are lined on the upper part with 100% flannel cotton, so it is like a blanket in your shoes. Additionally, they are fully insulated with Thinsulate, making them just so cozy to slip your foot into when you are bracing yourself for the elements outside after a huge snowfall. There is also a foam inner-sole that makes long walks very comfortable. I’ll also wear these on other non-snowy outdoor occasions, like if we visit a corn maze or apple orchard on a cold day where there may be lots of mud. And they are comfortable for those extended adventures!
One of the great parts of this boot are the laces that don’t need tying! This makes this boot extra easy. The trick is the “Eastland Knot,” and I learned how to tie it from on YouTube from Sincerely Molly- New England. I tie them about once a season, and they hold just right.
Also, I just love the look of this boot. It is rugged but soft. And most of all, it has a classic appeal. The stitching, sole, and colors will never go out of style and scream cozy season.
One point that is worth making, I would find a local L.L. Bean in your area and go in to try them on. That is because these boots don’t come in half-sizes, and depending on the thickness of the socks you use with these, it could alter your choice. Some advise to size-up, while others have found they size-down. It is up to you to try them for yourself before you buy.
If you’re not convinced yet, these boots will last you a long, long time. How do I know? While I’m only on my third year of relying on these boots, L.L. Bean offers a resoling service for very low-cost! So even after having them for years and years, you can have them repaired at a fraction of the cost of a new boot! This just can’t be beat.
Boots (Just Wet + Cold Weather)
There are days when it is rainy and cold; sidewalks are slippery. But you don’t want to wear rainboots for any number of reasons. Maybe you don’t want to carry another pair of shoes to put on once you are inside wherever you are going or maybe the boots are not comfortable to wear with the pants you planned for the day. The reason I don’t go for a traditional rainboot is how stiff they are around the ankles and shins. If there are more comfortable options in a traditional rainboot, I would love to know about them.
Sorel has so many great boot options, and they have an especially popular Chelsea boot that goes with work attire so seamlessly. I love pairing these boots with jeans, leggings and skirts. I have them in Quarry with Black stretch panels, but I’ve been wanting to add the Black option as well.
Here’s why I love these boots for days when there is no snow accumulation on the ground.
First, the ankle cut makes this boot comfortable and versatile. I’ve worn these with a pleated skirt as well as ripped jeans, and they can handle that range. My go-to is wearing these with leggings. I think what makes the boot so flexible for so many different looks is the modest rubber heel; it is just enough to add a special something without being too fancy about it.
Second, these are leather and waterproof, so they do the work of a rainboot. Soggy weather is nothing for these boots, and I’ve stepped in puddles and walked in heavy rain with these, and they are tough while still looking classy.
Last, they are comfortable. They have a snug fit at first, but when I bought them online, the comments warned that they would take a few weeks to break in, and I’m so glad I knew that. They feel great after just a bit of time. I love the ease of slipping these on quickly and heading out the door even if it is a quick dog walk or an extended city outing.
FAQs
When we moved to Chicago from the heat of Texas, we brought no coats with us or any winter gear. Our winter wardrobe consisted of a hoodie and flip-flops. We knew that we would have better luck shopping locally, and we had a few months before winter would show its icy, cold, wet, slushy self. Everyone bombarded us with advice, but I had more nuanced questions about the practicality of it all. So below are a few questions as well as the answers I’ve discovered from my time in the city.
- How do people not wear dress shoes during Chicago winters? Do people wear heavy boots all day? Now, this question may seem silly, but someone from a year-long warm weather climate who had never experienced “traditional” seasons like me may be very confused about this. A lot of people carry their nice shoes with them to work, school, wherever or they keep a pair of nice shoes at work. This is how my husband handles things. My kids are also learning about this trick as well, and they keep a nice pair of sneakers in their school locker to change if they need to wear their snow boots to school that day. This may seem like a lot of planning and another thing to remember, and if you’re not used to it, it can certainly feel like that.
- What about the radiators that get so hot you could roast a turkey on them? How do I handle all the layers of clothing when I am in and out of buildings, cars, etc.? Oh, the dreaded radiator that has no control settings. So, older buildings may have radiators, and the temperature is controlled by a system in the basement, etc. But if you live in an apartment with a radiator, you can’t exactly turn it off or on yourself. What this means is that you may have to open a window (even on a snowy day) if the radiator is blowing too fiercely. I will never forget having to crack a window in 19 degree weather for the night, and it worked out so wonderfully. The balance of the brutally cold air and the sauna-like heat from the old radiator was a perfect recipe for a good night. But the point is that dressing in layers is the best way to keep your body temperature at a healthy and comfortable state. I made the mistake of not dressing in layers during my job visit when I interviewed at the university where I teach, and I pretty much sweated my way through a large chunk of it.
- How do people use their cell phones while wearing mittens? I still haven’t figured this out. But I would love to hear what you know about this!