How To Wear A Dress In Winter When It’s Freezing Outside

Aren’t you tired of only wearing skinny jeans and a sweater during the entire winter season? When it’s freezing outside, it doesn’t sound fun to wear a dress for work or as a date night outfit. But with these styling tips, you will learn how to wear a dress in winter, even when it’s freezing outside.

Does that mean for 3 months of the year, you can only wear pants and boots?

Great news is there are many styling tips using your winter capsule wardrobe. Use your basic essentials to help you plan how to wear a dress in winter when it’s freezing outside.


How To Wear A Dress In Winter

From sweater dresses to over the knee boots, there are many cute capsule wardrobe essentials that you can mix and match with your favorite dresses in winter. Whether you want to wear a sheer summer dress or strapless dress, we’ve got you covered.

Where a dress in winter when traveling from cold to hot weather destination. With the appropriate layers, a dress in winter is a comfortable airport outfit for traveling in winter. Stay stylish and warm while wearing any dress style or silhouette.


Is it too cold to wear a dress in 50-degree weather?

In 50 degree weather, it is not too cold to wear a dress, especially if you winterize dresses with basic capsule wardrobe essentials.

When it comes to winterizing dresses, it’s up to your individual taste and style to achieve your desired look. The best place to start is to wear a proper coat.


What kind of coat to wear with a dress?

Go with a wool coat and a faux fur vest. Those basic essential items are always a great selection to wear with any dress in winter.

Not all coats will keep you warm, here are best base layer for cold weather to help you stay warm in a dress:

  • Wear long sleeve layer underneath.
  • Wear fleece lined tights or leggings instead of regular leggings.
  • Layer with scarf and coat over the dress.
  • Wear a slip dress to prevent static and sticking to your tights.
  • Wear over the knee boots rather than ankle boots.

If you have been putting aside your favorite dresses in winter, mix and match your winter capsule wardrobe essentials. It’s easy to stay cozy and cute throughout the entire winter.


How To Wear A Black Dress In The Winter

How To Wear A Black Dress In The Winter

source: @tiffanyallison7

In order to know how to wear a black dress in the winter, you can simply throw a faux fur vest over the top. Make sure that it is the same length as your dress.

In addition, accessorize with a wool felt fedora hat that will keep you warm and looking stylish. You can also wear heels or boots depending on the weather for the day.


Winter Dresses With Leggings

Winter Dresses With Leggings

source: @junesixtyfive

Winter dresses with thermal leggings is a classic outfit that everyone can easily digest. Whether you are wearing a midi length dress or mini length, pair it with sheer or opaque leggings and chic ankle boots.


How To Wear A Summer Dress In Winter

How To Wear A Summer Dress In Winter

source: @ciaraodoherty

Is it possible to wear a summer dress in winter?

Whether you choose a sleeveless chiffon mini dress or deep plunging neckline animal print silk dress, you don’t need to wait for next season.

Wear a simple neutral color ribbed turtleneck underneath the dress to give more coverage and to stay warm. Match your coat color with the top color tone to look chic and edgy at the same time.


Short Winter Dresses

Short Winter Dresses

source: @macystucke

The easiest way to wear short winter dresses is to wear tall boots. Whether they are over the knee length or just under the knee length, that choice is yours. Make sure to avoid ankle boots with bare legs.


How To Wear Maxi Dress In Winter

How To Wear Maxi Dress In Winter

source: @gigirella_

Everyone loves maxi dresses. They are so comfortable and make you look flawlessly feminine all season long. That doesn’t mean you can’t wear a maxi dress in winter.

Black background with rose floral printed chiffon maxi dresses is a pattern that you want to consider this winter. Simply wear fleece-lined tights with ankle boots and you are ready to go.


Dresses To Wear With Tights And Ankle Boots

Dresses To Wear With Tights And Ankle Boots

source: @mystyleandgrace

Do you want to wear an outfit that is work-friendly and ready for happy hour afterwards?

Then try a simple crewneck black shift dress with a long wool coat. Wearing tights and cute ankle boots adds a unique touch to your winter capsule wardrobe outfit.


How To Wear A Wrap Dress In Winter

How To Wear A Wrap Dress In Winter

source: @kimmeldr

Other than wearing a turtleneck, how to wear a wrap dress in winter?

Wrap dresses, especially a classy polka dot chiffon wrap dress, was so trendy all summer.

The best way to keep wearing your wrap dress this winter is to pair it with an oversized sweater over the top. This way it looks like you are wearing a separate skirt. It’s so cute and casual, perfect anytime from day to date night outfit.


Midi Dress In Winter

Midi Dress In Winter

source: @lydia_herfst

Midi dress in winter is an awful length that will make your ankles freeze. But this silhouette midi dress makes you look taller and chic with block heel ankle boots and skin color thermal leggings.


How To Wear Dresses In Winter And Stay Warm

How To Wear Dresses In Winter And Stay Warm

source: @the_stylish_eduga8r_190

It’s easy to wear black and white all winter long. Instead, add a fun pop color as your primary color palette in order to wear dresses in winter and stay warm.

Whether you are going with bright yellow or lipstick red color, always remember to layer your dress with tights and a classic long coat.


Floral Dress With Ankle Boots

Floral Dress With Ankle Boots

source: @beforeeesunrise

A floral dress makes everyone instantly look so pretty. It’s really easy to wear a floral print pattern during springtime.

For winter weather, you can still wear a floral dress with chic ankle boots. Make sure to pick a thicker and heavier fabric such as faux leather or velvet, rather than sheer chiffon material.


How To Wear Sleeveless Dress

How To Wear Sleeveless Dress

source: @brunatenorio

If you are attending a house party or special holiday event, you can wear a sleeveless dress during the winter season. Make sure to wear a long sleeve top to keep you warm. In addition, cover your neck with an oversized blanket scarf to stay cozy and stylish.


What To Wear Over A Strapless Dress

What To Wear Over A Strapless Dress

source: @sarahbtm

From spring to summer, strapless dresses are so versatile. You can easily make it casual or even date night ready. Whether you are wearing a mock neck top underneath or a sweatshirt over a strapless dress, it’s up to you.


Little Jackets To Wear Over Dresses

Little Jackets To Wear Over Dresses

source: @littleblackboots

Outerwear is always a great idea when you are wearing a dress in winter and it’s freezing outside. Instead of wearing a long wool coat, which makes you look bulky and heavy, how about a cute little jacket.

You can either wear a velvet, suede or even a faux leather moto jacket to keep warm.


What Length Coat To Wear With Dress

What Length Coat To Wear With Dress

source: @tati4fsn

From cropped length to maxi, there are so many options when it comes to deciding what length coat to wear with a dress in winter. To stay the warmest, it is best to stick with a long length.

As a result, you will look lean and taller. Make sure to brighten up your look with a light color long coat such as mint or blush color.


Other than sweater dresses with over the knee boots, it’s difficult to wear any dress outfit when it’s freezing outside. With these styling tips and tricks, you can easily wear a dress in winter without hesitation. Don’t wait for warmer weather to wear your favorite dress anymore. Start today by using your winter capsule wardrobe essentials to stay cozy and stylish when its cold outside.

What are your favorite ways to wear a dress in winter?

Share your styling tips with us!


fashion wanderer

How To Wear A Dress In Winter When It’s Freezing Outside

Soonjoo Uh

I graduated with a bachelors of fine arts degree in fashion design. I worked in the fashion industry as a lead designer for major brand name labels such as Stitch Fix, Urban Outfitters, Nordstrom, and Dillards. Now, I am the founder of the website Fashion Wanderer where I share current fashion trends, style tips and how to build a capsule wardrobe collection.

  1. 50 degrees is definitely too cold for me to wear a dress! Luckily, in South Texas, it’s only really cold about two months out of the year and gets below freezing for maybe a week. I like wearing leggings under my dresses to help combat the cold, but I didn’t know there’s such a thing as lined leggings! I’ll have to find some of those soon!!

  2. Oh, gosh, this is too funny! I have to say, I read the line about “when it’s 50 degrees out” and my mind jumped back to the days when it was regularly 50 degrees BELOW zero F windchill where I used to live! Def did not wear dresses in winter there, unless they were long and had lots of layers underneath!

  3. I love these dress looks for winter! I tend to avoid dresses in the winter but I need to not do that

  4. All of these looks are so great. Winter can be hard for wearing cute fashions and all of these dress outfits deliver.

  5. Great post and fab looks. for me it is all about a good pair of thick tights and a solid winter coat xx

  6. I have totally done all these things just so I can wear my dresses in the winter. Totally worth it!

  7. These winter dress outfits are pretty. Winter clothes wearing is one thing we need to do to look good and be careful and you have good tips!

  8. Lots of people do not think that you can wear a dress in the winter time. These are some great tips for being able to do that!

  9. What a simple idea – throwing a faux fur over your dress! That’s perfect for winter. Luckily I live in the south and we can get away with dresses and open toe shoes for longer than usual.

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