Dressing Cute in the Cold

Holiday Outfit with Cuddl Duds

Last month I attended an event hosted by CakeStyle, a Chicago-based personal shopping service. After some mingling, we sat down for a Q&A with the stylists, who wanted to know if we had any issues we needed help with. My hand shot up first, “I’ve got an issue,” I said, “How in the world do you look cute when it’s so cold out?”

Though I was born and raised in the North, three years of living down South undid my winter fashion sense to the point where I spent all of last winter in a puffy grey coat and jeans. It wasn’t cute, and I vowed to make a change this year. I’ve been keeping warm and relatively stylish with the help of CakeStyle along with a few winter essentials.

Tips for Staying Stylish in the Winter

I took my company’s holiday party as the perfect opportunity to put some of CakeStyle’s recommendations into action. Keep reading to find out how I pulled an outfit together.

The Base
Staying warm in the winter is all about layering. When it comes to braving the cold in a dress, you have two great options for staying warm: Tights and Cuddl Duds. I used to double up on tights, but I usually found I was still cold, so I took the extra step to add on a pair of tight black Cuddl Dud leggings that look like tights. And, of course, a pair of warm wool socks!

The Dress
You can really wear any dress when you have the proper base to keep you warm. This is the perfect opportunity to pull out dresses you typically wear in the spring or summer. In this case, I chose a classic black shiny strapless dress from The Express.

I paired a silver belt with this dress, making sure the buckle was in the back where no one could see. WIthout a belt, I find this dress is a bit too baggy and the belt gives it a little something extra. I also added a silver sparkly bracelet from Jewelmint.

Top It Off
Since my company is more casual, I decided to wear a thrifted royal blue cardigan from Lands’ End. I always think adding a casual cardigan on top of a party dress helps downplay the outfit especially if you’re concerned about looking too dressed up.

The Boots
I finished my outfit off with my favorite winter shoes: a pair of black suede Anne Klein boots that I’ve had for 7 years. If you choose to wear a heel or shoes that won’t exactly keep your feet warm, think about wearing practicial shoes to the location and change them once you get there. We all want to look stylish, but, let’s face it, no one wants to have cold feet.

Considering that I usually take my coat off when I get to wherever I’m going, I don’t put too much thought into my coat and I wear what keeps me warm. The only advice I would have is to choose a coat that matches the length of your dress. I tend to dislike wearing short coats with dresses and instead opt for a long wool coat. But, yes, just in case you were wondering, I did wear my puffy grey coat with this outfit.

Share Your Winter Style Tips

How do you stay warm in the winter? What’s the key to looking good once it just gets too cold? Share your thoughts!

Disclaimer: Cuddl Duds and Jewelmint items were sent by their respective companies for review. I was not compensated for this post nor required to share about this product. For more information, please view my Site Policies.

About Courtney Mirenzi

Courtney Mirenzi is the voice behind Those Graces. She has been named one of the 50 Most Fashionable People in Boston, one of The Boston Globe's Top Bloggers and favorite human of one of her cats. She loves red lipstick, hiking and traveling. (Find out more.)


  1. Awesome tips! I’m terrible at dressing for the cold. Usually around February I give up and live in hoodies. Its surprising to me that I don’t own a snuggie.

    Happy Holidays!

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