5 Ways to Wear a Dress in the Winter
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  • Writer's pictureBrenda

5 Ways to Wear a Dress in the Winter

Updated: Apr 20, 2023

With winter upon us, a lot of you may not be thinking about dresses right now. That may be one of the clothing items hidden all the way at the back of your closet. So many people pack up their cute summer dresses once the colder months approach but that does not necessarily have to be the case.

I have spoken many times on this blog about styling some of your favorite summer items during the winter season. From maxi dresses to mini skirts, it is possible to bring pieces of your summer wardrobe into your winter wardrobe.


In today’s blog post, I would be focusing on styling dresses during the winter. This might be for a holiday party, an office event or even for date night. Dresses can and should be worn throughout the year if you’re a sucker for them as much as I am. The key is in layering your dresses with the right items. If you are seeking different ways to style a dress for colder climates, do keep reading.

To start off, it’s important to begin with the right base. In this case, the right dress to add to your winter wardrobe. Let’s be honest, not all dresses are made the same and there are some you probably do not want to wear during the winter.

I would be sharing my favorite types of dresses to wear during the winter months. These are dresses which are easy to wear, easy to layer and easy to move around in because no one has to time to fuss over a maxi dress dragging around in the snow.

*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

i) Sweater dresses

These are probably the most popular of all winter dresses. They are made for winter, often being constructed from thicker and warmer fabrics such as wool and yarn. Wearing a sweater dress is a great way to stay stylish yet warm during the cold weather.

You could opt for a longer dress to protect your knees and also add a pair of leggings or tights underneath your dress for some extra warmth.

I have a post titled 8 ways to wear a sweater dress where you can get more outfit inspiration with regards to sweater dresses.

Get the look HERE

I also love this longer version with a turtleneck HERE

ii) Midi dresses

Midi dresses are truly that sweet spot when it comes to dresses you can wear in the winter. They’re long enough to be appropriate for the colder weather and short enough to not drag all across the snow when there’s a blizzard. You can also easily style them by adding layers on top such as a sweater as well as underneath (think black tights).

Get the look HERE

iii) Long sleeved dresses

Another great choice of dress to wear during the winter is a long-sleeved dress. The long sleeves would keep your arms protected from the cold while you deal with protecting the rest of your body. You could style them with a pair of knee-high boots if your dress is on the shorter side. You could also add a pair of fleece-lined tights for an extra layer of warmth.

Get the look HERE

I also love THIS OPTION which would add a pop of color to your winter wardrobe.

iv) Floral dresses

Yes, I know we’ve been conditioned to think that floral dresses are meant for the warmer months but who created this rule? The sight of florals on a gloomy winter day instantly brightens up my mood. You would be surprised by how many of your floral dresses you could pair with a leather jacket and tall boots to brave the cold. You can also easily layer them with a sweater on top of or underneath your dress.

Get the look HERE

Now that you know all of my favorite places to shop for dresses you can wear in the winter, let’s discuss styling them as well as other dresses. Even if you do not own any of the following dresses, feel free to use this as a guide you can refer to.

The goal is to give you ideas for creating stylish winter outfits with your favorite dresses. These could be summer dresses or winter dresses.

1) With an oversized sweater

The easiest way to wear a one of your summer dresses during the winter is by layer it with a chunky sweater. This would add some much-needed warmth to your outfit while keeping you looking stylish. Slip on a pair of ankle boots if your dress is longer or you could opt for a pair of knee boots if your dress is shorter.

Image source here

If it’s really cold outside, don’t forget your long coat and you’re ready to brave the cold weather.

If your dress is longer and you’re headed for a special occasion, you can also choose a pair of sheer tights. This would keep you looking elegant yet warm during your night out.

2) With a fitted sweater

Instead of wearing your sweater on the outside, try slipping it underneath your dress. This creates a more elegant look, especially if you’re working with a dainty dress such as a slip dress. A round neck or turtleneck sweater work well with this look. Make sure the color of your sweater compliments that of your dress.

Image source here

A thick sweater also works underneath if you're on the slim side and want to add some volume to your upper body. Complete your look with a pair of boots and a long line coat. You could also wear a denim jacket on top of your sweater + dress outfit if you’re going for a more casual look.

Image source here

3) With a puffy coat

I like to reserve my puffy coat (not faux fur coat) for less formal occasions. Puffy coats give a more casual vibe to an outfit and so they are a good idea if you’re headed to a casual event. The general rule is the longer your dress, the longer your puffy coat should be.

If you have a mini dress you’re itching to rock this winter, you could pair it with one of your puffy bomber jackets and add a pair of combat boots. This is a great choice of outfit if you’re heading for a night out with your girls.

Image source here

4) With a leather jacket

Sometimes, the winter weather pleasantly surprises us, and we get some warmer days. This is when pairing your dress with a black leather jacket is a good idea. Short dresses could be paired with knee boots and thick tights for a casual look.

Short boots could be paired with knee-high socks to create a chic preppy look that would still keep you warm. Long dresses could be paired with leggings or tights and a pair of ankle boots.

Image source here

5) With a trench coat

One of the best ways you can style a dress for a dressy event during the colder months is to choose a trench coat as outerwear. I suggest opting for a long dress with a long sleeve for maximum warmth. Add a pair of opaque tights underneath your dress for an extra layer of warmth.

You could wear a blazer on top of your dress before slipping on a classic trench coat. My favorite types of dresses to pair with a trench coat are pencil dresses, skater dresses and shift dresses.

Get the look HERE

And there we have it! % ways to wear a dress in winter! I hope I have provided you with some great style tips you can put into practice the next time you’re styling a dress in the winter. Remember that the secret is just in the additional layers.

Start with lighter layers all the way to the thickest one, (your outerwear). The easiest way to take a dress from summer to winter is by adding a sweater either underneath it or on top of your dress.

Choose longer dresses made from warmer materials if you don’t want to wear leggings or tights underneath your dress. Boots are your best friend and so you want to invest in a few great pairs to ensure you’re keeping warm yet stylish all season. Who says skinny jeans and pea coast are the only way to stay fancy this time of year?

I suggest you check out my post: 7 shoes to wear with dresses in the winter if you need some ideas on the types of boots to pair with your winter dress outfit.

For outfit ideas on what to wear to a formal dance, check out my post: 7+Outfits to Wear to a Formal Dance.

I also have a post titled 6 ways to wear a cardigan over a dress to provide you with some more winter wardrobe inspiration.

Going to be on TV for your first time, check out my post: 7 outfit ideas to wear for a TV interview.

Until the next post,



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