Midwest Winter Packing Guide: Stay Warm, Dry & Stylish

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There’s cold, and then there’s Midwest cold. Your Midwest winter packing guide needs to make sure you will look stylish but also stay warm.

In this guide, I’ll walk you through exactly what to wear in the Midwest in winter, from snow boots to thermal leggings.

This Midwest winter packing guide is here to help you stay stylish, warm, and totally prepared.

Here are some Midwest Winter Getaways: 14 Destinations For Your Bucket List for some inspiration.

Young expressive black woman having fun in winter outdoor. Article is about your Midwest winter packing guide.

**Midwest Winter Packing Guide: What’s the Weather Like in a Midwest Winter?**

Winter in the Midwest isn’t just chilly, it’s intense.

From about mid-November through March, you can expect temperatures that dip below freezing (and often below zero),

With biting winds that cut right through you, and snowstorms that appear out of nowhere.

Chicago in January hovers around 30°F during the day but can easily drop into the teens.

Head further north to Minneapolis or Fargo, and you’ll face single-digit highs and wind chills that take your breath away.

Even places like Ohio or Missouri, which may seem milder, can get snow and ice storms.

The point is: even if you’re just heading out for dinner or sightseeing in the city, you need serious outerwear.

Happy teenage girl showing thumbs up in winter

**The Right Coat Makes All the Difference**

If you only invest in one thing for your Midwest winter trip, make it a proper coat.

I’m talking about something insulated, long, and windproof, ideally with a hood.

Bonus points if it’s waterproof or water-resistant; you’ll thank me when you’re walking through sleet.

This Orolay Women’s Thickened Down Jacket is a cult favorite on Amazon for a reason.

It’s warm, practical, and surprisingly stylish, with lots of zippered pockets and a great fit.

For something longer and sleeker, I love the Eddie Bauer Women’s Sun Valley Down Parka, a classic that hits mid-thigh and handles brutal temps like a champ.

If you prefer a coat that packs down small (great for carry-on travel), try this Amazon Essentials Lightweight Long Puffer.

Afro american woman happy dressed for winter in long coat

**Thermal Base Layers: Your Best Friend**

What you wear under your outfit matters so much more than you think.

Start with a set like Thermajane Women’s Ultra Soft Thermal Long Johns. They’re soft, stretchy, and come in a bunch of colors.

Pair with thermal leggings like the BALEAF Fleece Lined Leggings, which are thick enough to wear on their own under a tunic or oversized sweater but warm enough for outdoor walks in the snow.

Asian girl in a cap from the skin of a wolf. Midwest winter packing guide

Midwest Winter Packing Guide: **Cozy Mid-Layers for Indoors and Out**

Once your base layer is sorted, add a cozy mid-layer.

A chunky knit sweater, fleece pullover, or even a lightweight down vest can make all the difference.

This Amazon Essentials Sherpa Fleece Pullover is affordable, cute, and works both indoors and outdoors.

I also love wearing a lightweight down vest like this one under my coat for extra core warmth without making my arms feel bulky.

**Snow Boots You Can Walk In**

Forget the fashion boots; when you’re dealing with snow, slush, or ice, you need waterproof footwear, insulated, that has serious grip.

These Columbia Women’s Ice Maiden II Snow Boots are warm, stylish, and built to last.

They’re tall enough to keep snow out, but not so heavy they feel clunky.

Make sure to pair them with Merino wool socks. Your toes will thank you, especially if you’re walking around outdoor markets or standing at a holiday festival.

Beautiful Woman Wearing Fashionable Winter Clothes (white down jacket, knitted stylish hat, sweater, leggings, mittens, felt boots) Outdoors.

Midswest Winter Packing Guide: Outfit Ideas for Every Month

December: Festive and Freezing

Start with a soft thermal base layer that keeps you warm without overheating.

Over that, throw on a chunky turtleneck sweater paired with fleece-lined leggings and a puffa coat.

Finish it off with waterproof snow boots, a cable knit beanie, a cozy scarf, and touchscreen gloves to keep everything toasty and practical.

For indoor gatherings, say, a holiday dinner with friends or family, go for something dressier but still warm enough for those quick outdoor dashes.

I love a long knit sweater dress over fleece-lined tights, then add a pair of ankle boots.

A wool-blend coat in a classic silhouette finishes the look and keeps me feeling polished, even when I’m shivering in the driveway.

For road trip days where you’re hopping in and out of the car, stopping in small snowy towns, or visiting a farm shop or two,

a thermal top, a cozy flannel shirt layered under a down vest, and either fleece-lined jeans or stretchy thermal joggers work perfectly.

If you are looking for some inspiration on where to go during the holidays, check out my Christmas in the Midwest: 15 Festive Holiday Destinations.

cozy layers, curly young woman in layered clothes with warm scarf and mittens on grey backdrop. Midwest winter packing guide.

January: The Deep Freeze

A thermal base layer is non-negotiable, with a cropped chunky sweater and a serious winter coat that works perfectly.

Thick wool socks keep my feet dry inside heavy-duty boots.

I love my SOREL Caribou boots for days like these; they’re a little bulky, but they’ll get you through the iciest sidewalks with confidence.

Here is a list of some inspiration for dressing in Chicago in winter.

If I’m spending the day inside a cabin reading by the fire, sipping tea, or watching the snow fall, I still want to feel cute while staying ultra comfy.

I’ll pull on a pair of fleece-lined joggers and a long-sleeve waffle knit pullover that feels like pajamas but looks just put-together enough.

Add some thick slipper socks like these cabin socks from MUK LUKS and maybe a chunky cardigan, and you’ve reached Midwest winter nirvana.

For something a bit more active, like a walk through a snowy park or a trail hike, gear up in a fleece-lined thermal top, insulated snow pants/bib, and a windproof Columbia jacket.

Columbia Newton Ridge hiking boots are ideal if you’ll be trekking through snow or mud. Add a beanie and gloves, and you’re ready for a peaceful (but chilly!) nature escape.

A young woman with long hair wears a warm black coat and beanie while standing on a stone pathway surrounded by snow.

February: Snowy Romance

February can go either way, full-on snowstorm or mild(ish) and slushy. It’s also the perfect time to sneak in a romantic weekend or a cozy getaway.

For a Valentine’s dinner or a date night out, I like to dress up just a little.

A long-sleeve knit dress feels flirty but keeps you warm, especially layered with fleece-lined tights.

Add a pair of knee-high boots and a belted wool coat, and you’re winter-date ready.

For something more casual, say, a coffee date, ice skating, or exploring a new town I like layering a soft thermal top with a plaid shacket and lightweight vest.

It keeps you mobile and stylish without overheating.

On mild days when you’re out antiquing or browsing bookstores, go for a classic look.

A soft mock neck sweater, fleece-lined skinny jeans, and a cozy wrap coat or long puffer.

Waterproof Chelsea boots with a tread are stylish enough for lunch or a museum stop, but practical for walking snowy sidewalks.

Happy couple near a Christmas tree. Christmas Eve. Midwest winter packing guide

Midwest Winter Packing Guide: Essentials Packing List

Here are my tips on how to pack lightly. using a carry-on when traveling in the Midwest. And WHY it is almost a necessity!

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday. It is made of lightweight aluminum and is so easy to use.

I never leave home on a trip without a disposable water bottle.

Then this collapsible silicone foldable water bottle would work well for you as well.

This foldable water-resistant backpack would be great for a daily go-pack.

These quick-dry slip-on Aqua shoes will be useful if visiting indoor waterparks.

These men’s quick-dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in many lens colors and frame designs and are extremely affordable, too.

If you like aviator-style sunglasses, these polarized aviators may interest you.

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