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:

Build-a-Bear, But With Clothes:

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.