How to Wear a Dress in Winter and Stay Warm

Winter weather has a way of zapping the excitement out of our wardrobe. We get cold; we get lazy and we end up wearing whatever works. Generally, that’s a bulky sweater and jeans. If you’re anything like me, this method eliminates half my closet. Dresses are my favorite thing to wear. So, why wait for spring to arrive? I prefer to restyle and keep my favorite dresses in rotation. Wondering how to wear a dress in winter and stay warm? Here are a few methods I swear by…

Reporting From the Frozen Tundra

Before we unpack exactly how to wear a dress in winter, I want to share a quick story. It explains why I’m what you could call a reluctant expert on the topic.

For those who are new here, I used to work in television news. One of those jobs involved covering severe weather in the Green Bay, Wisconsin. Let’s just say there’s a reason they call Lambeau Field the “Frozen Tundra.”

I can’t tell you how many times I went to work in a dress, only to be reporting live from a snowbank that evening. When you need to dress professionally [but warm] on a daily basis, you pick up a few tips and tricks. I talk more about dressing for the camera in this post.

Dress | Coat (similar) | Boots | Lower Cost Boot (Only $79!) 

How to Wear a Dress in Winter

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Layering Techniques for Winter Dresses

It’s definitely a balancing act… Wearing dresses in the colder months requires layering up, but doing so without adding bulk. The key is effective layering. Thin, high-quality layers work wonders when it comes to staying cozy and comfortable. Here is my method, step-by-step…

How to Wear a Dress in Winter: My Formula

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1)  Start with a Great Base

Your base can either go over your dress, or it might be the dress. Learning how to wear a dress in winter means learning about fabrication. More precisely, it means reading fabric labels carefully, so you can choose the ones with maximum warming potential. For example, while you may have stumbled upon blog posts encouraging you to wear a silky slip dress with a chunky cardigan, that’s not the best approach for warmth.

It’s cute… it’s trendy. However, it’s not realistic for those of us in the Midwest (especially not in February). To wear a dress in the winter and stay cozy, it’s helpful if the dress itself has some warming properties. For instance, long sleeve knit or sweater dresses (like the style I’m wearing) are always a great choice. Look for dresses in thicker fabrics or seek out fabrics like Merino wool or cashmere blends, like this dress.

If the dress isn’t your base layer, consider what you might wear over or under it. With a base layer, we’re trying to create a second skin that draws any sweat away from our body. This means, you’re looking for fabrics with moisture wicking properties. However, much of this gear can look too “athletic” to pair with dresses. Since you probably won’t be hiking up a mountain at work, a slim-fitting merino wool or cashmere turtleneck is a great alternative. Quince is my go-to brand for affordable cashmere (you can find my full review of it here).

Fleece-Lined Tights

2) Opt for Fleece-Lined tights

Okay, these are a game-changer! One can only handle so many teeth-chattering, freezing live reports. As a result, I discovered a glorious solution in fleece-lined tights. They provide so much warmth, but unlike many fleece-lined leggings, they don’t add bulk. In my opinion, there is a difference. This pair (Amazon find) is the sleekest I’ve found, but sooooo warm. I love how they give the look of a sheer nylon.

On really cold days, I top the fleece-lined tights with a pair of wool ankle socks before slipping into my boots.

That brings me to our next step…

3) Build Warmth With Boots

Boots – They are critical for warmth! In fact, the first thing I tell anyone who is asking how to wear a dress in winter without freezing is to invest in a great boot. Yes, tights (especially those fleece-lined ones) help, but nothing protects your legs quite like a boot. You honestly don’t feel the cold at all.

What should you look for in a winter boot?

Since we’re pairing our boot with a winter dress, we don’t want that chunky “outdoorsy” look. Rather, you want a sleek, pointed-toe or almond shape toe which visually extends your leg line. Kitten heel are very “of the moment” and offer an elegant silhouette. It’s also helpful to find a waterproof or water-resistant style. Knee-high styles will give you the most warmth.

For example, this pair from Aerosoles is a great bargain ($79 originally $230). It’s a water-friendly genuine suede. The Stevie knee-high boot from J.Crew is in my cart right now. It has a loose, relaxed shaft giving it a fresh and modern look. Quick note: Because the Stevie has a wider circumference, those with really slim legs may find it sloppy looking. In contrast, those of us with wide calves can rejoice – plenty of room! The shaft might be a bit too tall for the 5′ and under crowd, but I’m going to give it a go.

I’m wearing the waterproof Laura boot from Italeau. It’s a older style, so there’s only a few sizes remaining.

4) The “Sandwich Layer”

I’ve heard this called a number of things, but I think “sandwich layer” is pretty apt. Once you build warmth with a base layer, you want to seal it beneath a top layer. A cardigan, sweater, or sleek jacket acts much like the bread of a sandwich – keeping all the good stuff inside.

For the sandwich layer, think about what will be visible at the neckline and hem. You want colors and textures that complement one another, but also items that add dimension. I find leather jackets work really well (this one is my current fav), because they add textural variety.

Dress | Boots | Fleece-Lined Tights | Bag | Blazer (similar)

5) Final Outer Layer

Finally, it’s time to top our look with a sleek and stylish coat. It’s helpful to think about proportions when choosing your top layer. For example, with shorter dresses a longline coat will help balance the look, while a more traditional length is perfect for midi styles. I’m linking a few petite-friendly coats I love below.

Make sure to choose a piece that matches the formality of your dress. I prefer well-tailored styles or traditional trench coat cuts. However, I have seen darling examples of a dresses styled with a fun vest. Ultimately, it’s up to you to choose how to wear a dress in winter. I’ve addressed function, but style is deeply personal!

How to Wear a Dress in Winter 

Do you have a go-to method that makes dresses more wearable in the winter? Please share it in the comments!