28 Winter Wardrobe Essentials


Today is a bit of a “Wardrobe 101”. You see as much as I hate the cold Chicago winters, I absolutely love dressing for them. I just love, love, love to layer. So I’m sharing the 28 must have pieces every woman needs to round out a versatile wardrobe for winter. From cozy parkas to edgy leather to go-to denim and even accessories, we’ve got you covered from outerwear to sweaters and denim to shoes and bags. 

And these pieces are so easy to mix and match that you’ll be able to create countless outfits the whole season through. These are such classic pieces that you’ll find yourself turning to them time and again throughout the winter months. Many of them will even transition to the warmer and transitional seasons as well! So scroll on for my favorite winter necessities. I’ve literally got you covered from head to toe!

The Winter Wardrobe Rundown.

Winter Parkas:

Trench Coats:

Leather Jackets:




Simple Striped Sweater:

Neutral Sweater:

Turtleneck Sweater:

Cozy Cardigans:


Essential Hoodies:

Layering Tees:

The Top Tops:

Leather (and faux) Leggings:

Dark Wash Skinny Jeans:

Distressed Skinnies:

Black Skinnies:

Sweater Dresses:

Winter Boots:

Over-the-Knee Boots:

Wear Anywhere Booties

Cozy Shearling Boots and Booties:

Casual Kicks:

Falling for Flats:

Carryalls and Totes:

The Perfect Crossbody

Classic Necklaces:

Keep You Warm Socks:

What are your favorite winter essentials?


Looking for Something?