How To Dress In The Dead Of Winter

I didn’t grow up in a very cold climate (East Coast US) but I had no idea how to dress for winter, and therefore, thought I hated it. Fast forward 20 years, and I’m living in Chicago. The Windy City, next to a giant lake that regularly forms an icy crust through the winter months. 

And here I am, loving clothes even more today than I did as a child. But I’m just not willing to give up on the joy of styling an outfit just because I live a little South of the frozen tundra. So like any good Millennial I turned to YouTube to teach me how to enjoy Wintery Fashion and was promptly crushed.

“Wear a cute jegging with a long sweater, ankle boots (BARE ANKLES?!) and a cute coat!” they said. 

Obviously this is a cute look, but anyone suggesting bare ankles has not truly experienced an actual Winter season. 

So I quizzed my fashionable friends with experience in colder climates, read up on standard styles in colder European countries and finally, experimented on my own with a good Chicago Winter.

I’ve created a complete list of basics. I’m also going to show you 5 of my favorite looks that incorporate the use of basic base layers discreetly but effectively. 

Winter’s 5 Basics For Success:


1. Base layer leggings and tights. I prefer Patagonia wool. It’s not itchy and obviously, a great insulator. There are many options out there, but I haven’t ever heard of a synthetic option that is as warm as wool or wool blends.


2. Wool socks. Of varying thicknesses and lengths (crew is normally good but sometimes a knee-high is really helpful for shorter pants where wind blows up from the open ankle).


3. Tight layering tops, preferably in breathable cotton, wool blend or even cashmere. Bodysuits can work well. I prefer lower scoop necks or deep-v so that the layer you’re wearing on top is the only thing visible.


4. Boots. Practical snow boots as needed, but then also ankle or higher boots of any style you prefer (usually black or brown, or a bright color for contrast). So long as they include substantial grips (which also add height) on the sole -- you don’t have time to be slipping and sliding on ice, slush or rain-slicked streets. Consider looking up your area’s typical winter weather -- like how many days are usually rainy, versus snow or dry, so you can decide if leather is a good option or not.


5. And the final cherry on top: A coat that is RATED to be warm in your area’s temperatures. Stores like REI, Patagonia, LL Bean and more will often give a temperature rating to their heavy winter coats. Without this you truly cannot know with confidence that you can wear a normal winter outfit underneath and be sufficiently warm. Your typical Target coat is gonna need about 15 layers underneath to compete with a decent long puffer rated to keep you warm down to 5 degrees, you know?

Build-a-Bear, But With Clothes:


1. A gorgeous dress, lightweight (yes even summery) or warmer, layered with a turtleneck (and base layer top beneath if needed) and necklace(s) over the turtleneck to accentuate the neckline. Wool tights and/or base leggings can be worn beneath, and with boots, you’re all set for an easy femme look without any visual bulk.


2. Thick corduroy pants with crew or knee high wool socks at the ankle. Boots and a structured, cropped sweater over a base layer top. 


3. High waisted, wide leg denim. Base layer leggings underneath, with crew or knee high wool socks, boots and a body suit top layered with a button-down flannel you tie off at the waist or tuck in for definition.


4. A cute jumper or corduroy overall dress is so flexible for winter layering. You can put on a super warm, floppy sweater underneath and still get the structured lines of the jumper. Tights or even leggings UNDER tights for extra warmth will round out this look with clean lines and minimal bulk.


5. The last look can actually include your favorite pair of very slim fitting pants or stretchy sweater skirt from the fall season because you can wear your tights underneath for added warmth that’s also supportive in the ways all tights are. The top can then be a bulkier sweater or blazer over a thinner top because you’ll have your boots (maybe something higher to the knee?) and a very warm coat to go over it all. Once you’re back inside again, the blazer or sweater can be removed if you’re toasty enough in your tights, skirt/slim pants and top. 

These outfits get us the good clean lines and minimal bulk we want, but still keep you so cozy warm. After all, no one wants to look like the little kid from A Christmas Story, so bundled he can’t get up once he falls in the snow. 

Styling yourself in the winter is all about staying true to your personal aesthetic despite the extra challenges of layering. The cold shouldn’t stop you from being you. Embrace all of that wintery mix with your favorite looks, layered thoughtfully. 


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