How to Wear a Dress in Winter: Tips & Ideas for Cold Weather

Wondering how to wear a dress in winter? I’m sharing exactly how to rock a dress in the colder months, and how to wear a summer dress in winter so you can enjoy summer dresses year round! 

Graphic of four different ways to style a dress in the Winter.

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How To Wear A Dress In Winter 101

Don’t let cold weather convince you that you can’t wear a dress in winter! Wearing a dress when temperatures drop might not be your go-to, but there are plenty of holidays, celebrations, and other festive occasions worth getting dressed up for. Ahead, I’m sharing styling advice for exactly how to wear a dress in winter. 

This style guide will have you reaching for dresses all winter long. So, if you don’t already have a few dresses on rotation in your winter wardrobe, you will now. 

Is it OK to wear a dress in the winter?

You can absolutely wear a dress in winter, the key is to choose winter-appropriate styles (such as a sweater dress). Or you can wear your summer dresses in the winter by sticking with certain styles then adding cozy layers, tights, and boots.

Even though the temperatures are cooler, there are plenty of dress styles that will help you look chic and put-together while staying cold weather appropriate. Read on to learn more! 

Opt For A Sweater Dress

Christal wearing a grey sweater dress and a black cardigan with tall black boots.

get the look:

The best way to wear a dress in winter is to go with a winter-appropriate style like a knit or ribbed dress or sweater dress style. Sweater dresses are the original cold weather dress, so it’s hard to go wrong with this winter wardrobe staple.

There are countless sweater dresses to choose from, whether you go for mini, midi, or maxi length silhouettes or wool, cashmere, and cotton fabrics. 

In this look, I’ve styled a ribbed knit midi dress with a fitted black cardigan to give the outfit more dimension and another warm layer. Because the dress is shorter, hitting just at my knees, I’ve opted for these gorgeous Poppy Barley Toujours knee-high boots that will cover the rest of my legs.

Graphic showing how to wear a summer dress in the winter.

How To Wear A Summer Dress in Winter

Alternatively, if you want to put your summer dresses to good use in the winter (or year-round), here’s how I recommend you do just that!

Tip 1: Layer Over

get the look:

For this look, I’m wearing a classic spring and summer floral midi dress with flouncy sleeves and girly silhouette (the dress is from Evernew but sold out, I’ve linked similar above). With the help of a sweater, my summer dress is transformed into a look I can wear through fall and winter. 

To get the look, simply layer a warm knit sweater over a midi-length summer dress, tucking it in with an ‘invisible’ belt to give the sweater more shape (learn more about how to wear a sweater over a dress here).

And don’t forget the power of outerwear and footwear! I then threw my Quince leather jacket over my shoulders, added my knee-high boots, and grabbed a black shoulder bag to complete the look.

Winter-appropriate outerwear adds an extra layer of warmth and makes your outfit look well-styled for the season. Your summer dresses will instantly feel more cold-weather appropriate when worn with a jacket, wool coat, or trench coat. 

Tip 2: Layer Under

Christal wearing a black slip dress with a long sleeve tee under and black Chelsea boots.

get the look:


The art of how to wear dress in winter all comes down to layering. And while layering over your dress is a popular method for getting more life out of your summer dresses, come winter, don’t forget that you can layer under, too.

Slip dresses or sleeveless dresses make the perfect base for adding a thin long sleeve (like I’m wearing here) or lightweight turtleneck underneath. Pairing it with a lighter top will avoid adding awkward bulk to the outfit or making the dress look odd.

In this outfit inspo, I’ve added a matching long-sleeved top under my black slip dress, creating the illusion that the dress has long sleeves. Chelsea boots pair perfectly with maxi-length dresses in the winter, but you could also opt for heeled ankle boots or combat boots.

Seal in the warmth even further by adding a vest or jacket on top as an extra layer. 

Tip 3: Opt For Tights

What’s another way to wear a dress in winter? Try tights. Tights or thick pantyhose are a foolproof pairing for dresses that add warmth to your lower half.

Tights are a must if you’re wearing a shorter dress in winter. If you opt for a mini or midi dress, make sure whichever tights you wear complement the dress. For some dresses, you’ll want sheer tights. But if you can, go for opaque fleece-lined tights to keep your legs nice and warm.  

Tights can be worn with longer-length dresses too, even if you can’t see them. If you’re wearing a long dress, layer thermal tights or even leggings under knee-high boots for more coverage.  

Tip 4: Tall Boots Are Your Friend

Christal wearing a floral dress with black boots and a black sweater.

get the look:

Switching out your sneakers and ankle boots for knee-high boots is the easiest way to make your summer dress more winter-appropriate. These sleek, taller boots not only make any dress winter-ready, but they’re also one of fashion’s most-loved trends. A win-win for when you want to look chic and stylish in colder weather.

Flat boots, block-heeled boots, or even knee-high cowboy boots are perfect for casual outings when you’ll be doing a lot of walking. For a dressier vibe, high-heeled and pointed-toe boots – ideally in leather, suede, or embossed leather – are a great option. 

I’ve opted for a pair of black leather knee-high boots for this look. Additionally, the black boots add a nice contrast against the floral-patterned summer dress, giving it more of a winter vibe.

Tip 5: Avoid Neon & Summer Fabrics

A graphic of Christal showing what dress style not to wear in the winter.

As you’ve seen, you don’t need to say goodbye to all of your favorite summer dresses once winter rolls around! But there are still certain dresses you should avoid. Here are my top tips for choosing the right summer dress to wear in winter:

  1. Stay away from overtly bright colors and tropical prints: you’ll avoid looking out of season.
  2. Instead, choose neutral hues and subtle floral patterns: these look better in the colder months. You can still wear light colors, like white and cream, by intermixing them with dark tones or suede and leather accessories.
  3. Avoid sheer, crochet, linen, and cotton gauze dresses: these breezy fabrics won’t keep you warm in cold weather. Any cover-up dresses or sundresses that look like they should be worn on vacation or at the beach are a no-no. 

If your summer dress passes these criteria, it’s ready to be worn this winter!

What to wear with a dress to not be cold?

When wearing a dress in winter, here’s what you can wear to not be cold:

  • layer a warm knit sweater or cardigan over your dress
  • wear tights under your dress – fleece-lined or thick tights are best
  • wear a long sleeve top or thin turtleneck under your dress
  • add warm outerwear like a shearling-lined leather jacket, long wool coat, or trench coat
  • wear ankle boots, knee-high boots, or over-the-knee boots


I hope you have enjoyed these practical tips for how to wear a dress in winter. This style guide shows that with proper layering, you can wear dresses all winter long (and stay warm doing it).

Before you tuck your summer dresses in the back of your closet for the season, consider giving them a second life and styling them for the colder months. You’ll be surprised how seamlessly they layer with the rest of your winter wardrobe!


More Style Guides You’ll Love:

How To Style a Sweater Dress with Boots: 10+ Looks I Love

Effortlessly Cute Winter Outfits For Brunch & Beyond

Classy Winter Date Night Outfit Ideas You’ll Love

The Best Shoes To Wear With Sweater Dresses + Chic Outfit Ideas

How To Wear A Sweater Over Dress: Chic Outfits + Styling Tips!

16+ Classy Christmas Outfits To Copy This Holiday Season


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