It’s the time of year where new coworkers or neighbors from sunny places start to text you and say, “I’m getting scared for winter. What do I need to buy?” Hopefully, this will save you some time and you can shoot them the link to this post haha. Welcome to the hot girl’s guide to Midwestern winter!

There are two main areas of focus to survive and thrive: what you do at home, and what you wear when not at home.

Not At Home

I would say about 70-80% of the time, you can wear shorter puffers, UGGs, all that jazz. Winter really isn’t bad, until it is. To properly dress for that type of winter when leaving home, I’d like you to recall the song “Heads, Shoulders, Knees and Toes.”

Those are our focus points for how to dress, especially on the negative days!

Head

People really overlook how important headgear is for staying warm. A hood does not cut it all the time! Of course, you have your beanies. I look horrible in beanies and prefer a knit bonnet a la Little Women. I also recommend some sort of ear warmer, whether it’s ear muffs or a headband-like shape. Balaclavas are also extremely helpful when the wind is biting and snow may be blowing up and into your face. Scarves can be helpful for the neck gap as well, but honestly I use those more for a pop of color and have my headgear serve as the functional part.

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Shoulders

Layering is the name of the game when it comes to warmth. People swear by Uniqlo HeatTech. I’ve heard good things about the Intimissimi cashmere tops for more feminine layers underneath sweaters and cardigans. I also like the double lined tees from Abercrombie. Even if it’s just a plain old long sleeve, be prepared to layer underneath things. I personally run super hot, so I will only mega layer a few days of the year (granted, whenever the Extreme Cold Warnings come out, I usually plan to stay home.) I am grateful for all the layers I have to ensure my warmth on the days I am forced out into the abyss. Taking some liberties with “shoulder” to now discuss gloves. My apparently hot take is that as long as you’re wearing gloves, it doesn’t matter if they’re $5 Old Navy gloves or North Face ones. Have gloves on, keep your hands in your parka pockets, and you’ll be fine. And a PSA: the “tech friendly” ones won’t work if you have a glass screen protector on, so I don’t even bother. My phone can wait ’til I make it inside to warmth.

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Knees

Bottoms are very much so dealer’s choice depending on where you’re going. Only you know the office formality level, and if you’re new, I’d ask around for typical “cold day” dress codes. Sometimes it appears to be relaxed just to get you into the office! Lots of my in-office friends wear fleece-lined leggings with oversized sweaters (layers underneath, ofc) throughout winter. I’d recommend you own a pair or two even if it won’t fly for work as they’re a staple. If you’re needing to wear nicer, formal outfits to the office, definitely get some thick tights. They even make fleece-lined tights! Wear them under trousers, skirts, you name it for an added layer. I have worn the Noosh ones underneath jeans before! Despite what some people on the internet will tell you, Chicago does not get blizzard-level snow, and I do not think snow pants are necessary for most of the Midwest. If you’re on the lake effect side of the lake, however… not a bad idea.

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Toes

In the nicest way possible, your UGGs will not do shit when there is black ice or a foot of snow on the sidewalks. You will slip and slide and likely fall. I have seen it nearly every day there is precipitation on the ground during winter. You need traction, waterproof fabric and warmth. There is no “best” snow boot, so don’t listen to anyone who tells you otherwise. It’s personal preference for a lace up versus zip up boot. Mine are zips and I am so grateful for that fact! You won’t know what works best for your specific foot and walk until you try pairs on!!! If it were me, I’d go to a Nordstrom Rack and just try on pair after pair, walking down the aisles a bit to see what fits your foot. And remember, try them on with thick wool socks to really know if you have enough room. Speaking of socks, your snow boots will not be warm enough for 20+ minute walks without wool socks. People love Bombas, but I think my Uniqlo and Amazon ones work fine.

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One specific winter must-have that make up multiple of the above categories but needs its own moment to shine:

Parka

Similarly to snow boots, there is no one “best” parka for winter. Canada Gooses are nice, but I don’t think they’re really much warmer than others that are a fraction of the cost. I polled my group chat of Chicagoans who commute on snowy and frigid mornings, and the common themes are Aritzia, North Face, Columbia and Lululemon. The one thing that you need in a parka is LENGTH. Below the knee MINIMUM. I know, I know. It’s like you’re wearing a sleeping bag. It’s not cute. If you are getting in and out of a car for work, maybe you can handle the ones that hit at your waist. If you are walking or taking public transit, heed my warning and get a long puffer parka. I have one that hits at the knee from North Face (10 years old and still going strong with the down filling), as well as an ankle length. Parkas are not the “cute” winter coat, they are what will keep you warm on the mornings where temperatures are negative and there are frostbite warnings out. Get a fun color or patterned scarves to add some “cute” into the Michelin Man of it all. This is definitely the category to invest in, btw. Get the cheaper versions of all the above items and spend the money on one good quality parka that will last you years and years.

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me in my trusty north face parka in line for the kelsea ballerini concert because I couldn’t abandon my outfit idea despite the negative temps

At Home

Staying at home during Midwestern winter is downright delightful, if you know how to play it. Even on days you’re venturing out of the house, what you do when at home can make or break your mood.

Hygge

Add some hygge into your space in preparation for winter. It’s easier during the holidays when you have things decorated and festive. But even in January onward, make things feel special. Burn a candle when you’re home. Reorganize your closets. Bake some cookies. Run a simmer pot. Get some new throw pillows or a faux fur throw. In short, make your home somewhere you want to cuddle up and feel safe in! Far easier to do this ahead of a big winter storm than having to do errands during it.

Pantry Prep

I like to go through my nonperishables in my pantry and ensure I have soups, pastas, rice, etc. enough to tide me over if a storm rolls in and I don’t want to leave the house for a few days. I have my shelves organized by year of expiration, so the top one is full of 2028+, and the lower eye-level shelves are ones with quicker expirations for me to use this winter. If you don’t already, get a few things to have on hand!

Skincare + Lipcare

Even if you’re not a dry skin girlie like me, winter can wreak havoc on your skin and lips. Adding moisture into your normal summer routine is a MUST! Some favorite products of mine include the Dieux moisturizer, Laneige Milky Toner, and the Skinfix Barrier Cream. I increase the amount of product I use in winter, as my skin dries out even quicker than usual. I do not consider my moisturizer “on” until my face looks like a glazed doughnut. I finish off my nighttime routine with some drops of oil to “lock in” the moisture as well. On the lip front, I love the Paula’s Choice lip treatments. They now have a tinted version as well! I love the Tower28 Lip Softies as well, as it feels more like a gloss with the color and texture, but functions like a chapstick. Always nice to throw on a Laneige lip mask at night as well!

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Sunrise Alarm Clock

I didn’t know the impact a sunrise alarm clock would have on me, my routine and my sleep habits until I got my Hatch. There are a number of cheaper alternatives, like and even just timed sunrise lightbulbs, but the principle is the same. You slowly wake up to “sunrise,” despite the fact that it’s pitch black out. This helps you ease slowly out of REM sleep versus waking up abruptly during it with a traditional alarm. You feel less tired when waking up and it truly makes all the difference in getting a good morning routine going in the depths of winter.

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Robe + Slippers

You’re going to want to have a robe and slippers laid out for you to put on the second you escape the warm cocoon of your bed on the cold mornings. I have my robe draped across a side table and my slippers waiting for me to step into on the side of the bed! Avoiding the “cold” feeling also helps me stay on my morning routine and feel happier being awake while the sun is still down. Any robe and slippers will do (as long as they’re warm and closed toed), but I’m partial to my Barefoot Dreams robe and my UGG slippers.

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Plans

The biggest thing you can do for your mental health during winter is making plans. Plan out your week if you work from home. Create a routine for yourself in the mornings, even if you’re not logging on to WFH until 9am. Structure and schedule is good for your mental!! In your personal life, plans also make a big difference. Host your friends, or go to theirs if you don’t want to get “ready” in the cold. Schedule a workout just to be around other humans and leave the house. I like to have standing dinner plans with friends each week as well! On a larger scale, having plans to travel somewhere slightly warmer during winter can also be a light at the end of the tunnel. Any of your family or friends live somewhere warm? Take a long weekend to visit them! I try to have one trip planned per month after Christmas. To me, winter is cute and nostalgic and enjoyable until New Year’s. I need the mental boost after that!

From one Midwestern hot girl to another, happy almost winter and stay warm!!!

xoxo Caitlin