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

5 Stylish Ways to Wear a Maxi Dress in the Winter

Updated: Mar 20

Maxi dresses are very versatile and one of those clothing items you can transition from summer to fall and eventually winter. The styling of a maxi dress in the winter is very similar to how you would style a maxi skirt. It boils down to proper layering.

In order to layer your outfits without adding unnecessary bulk, it’s important to start with a great base. I’m talking thermal leggings, good quality boots and warm sweaters. Proper coats and jackets are also important in order to stay warm in the cold weather.


In today’s blog post, I would be giving you ideas on how to transform your summer dresses into outfits you can wear in the colder weather. You don’t need to buy a ton of new items in order to crate the perfect winter wardrobe. It’s important to know how to get the most out of your clothing in this economy.

I think it’s important that I start this post by sharing some great options of basics you want to ensure you own before styling your maxi dress for the winter. These items would be necessary to achieve a stylish yet warm look with your long dress during the winter months.

*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) Thermal leggings

A pair of thermal leggings could be the difference between your knees freezing or not. Adding a pair of leggings lined with fleece is a great way to keep wearing leggings into the winter. This also works if you have a long skirt you wish to wear during the winter weather. THESE fleece lined leggings are very highly rated and would be easy to slip under your winter maxi outfit.

ii) A leather jacket

I have spoken many times on this blog about the importance of investing in a proper leather jacket. It may set you back a little financially but in the long term, it’s a great fashion investment. When it’s not -40 outside, you could thrown on a leather jacket on top of your maxi dress to create a sleek winter outfit.

THIS leather jacket by All Saints is a classic you could keep in your wardrobe for many years.

iii) A maxi sweater dress

Sometimes, it’s just easier to opt for a maxi sweater dress than recycle a summer maxi dress. This would save you an extra layer as sweater dresses tend to have long sleeves. A long dress could be paired with ankle boots and a warm long coat for a stylish winter outfit. You could also opt for a pair of tights for extra warmth instead of thermal leggings.

THIS sweater dress is an example of a great winter maxi dress that would work great during the colder months.

iv) Long coat

I recently posted about styling long coats with dresses during the winter months. Adding a long coat such as a longline wool coat or a trench coat to your dress is the best way to elevate your cold weather outfit. Check out my blog post: The 7 best coats and jackets to wear with dresses for a whole list of different coats to pair with different dresses.

THIS Ralph Lauren puffer coat is both sleek as well as super warm.

v) A pair of boots

When you’re working with a long dress during the winter season, the easiest option is a pair of ankle boots. This is because they’re really easy to slip on and most of your dress would be hiding your feet either way.

Opt for flat ankle boots for less formal events and a pair of heeled ankle boots for special occasions. Knee boots could also be worn if you want more of your legs to be kept warm.

THESE sleek black ankle boots by Marc Fisher would be a stylish way to wear your maxi dress in the winter.

Now that you know the 5 important items o own in order to make a maxi dress outfit work in the winter, let’s dive into the best way to style yourself. The ideas and different styles presented would be very similar to my blog post: How to wear maxi dresses in the Fall. I suggest you check it out to get some more outfit inspiration.

The good news is you most likely already own most of the items listed. It’s just a matter of styling them to create chic looks.

1) Wear a sweater on top

Probably one of my favorite ways of turning my Summer maxi dresses into Fall maxi dresses is by adding one of my oversized sweaters on top of it. The sweater does not have to be oversized but a looser sweater does work best for this style.

Your maxi gown now looks more like a long skirt since the top part is covered and I have already talked about choosing your footwear to avoid looking frumpy.

Image source here

2) Wear a sweater underneath

During the cooler months, a perfect way to look chic but stay warm is by adding a sweater underneath your maxi dress this time. A thinner sweater should be used here instead of a chunky one made from heavier fabrics to avoid looking bulky up top.

I personally prefer to go with a thin black or white turtleneck. A sweater in a neutral color is preferable, especially if your maxi dress has some bold colors on it already.

Get the look HERE

3) Add a leather jacket

Instantly adds some sass to your maxi dress outfit with a leather jacket. A black leather jacket is your safest bet as it goes with everything. A brown biker jacket could also work nicely with your knit maxi dress and I even talked more about styling one HERE. A lined leather jacket is a very good choice to go with if you catch cold easily.

Image source here

4) Add a thick blazer

A well-structured blazer can hold you in the right place and is one of the most versatile pieces. If you wish to look a little more formal in your maxi dress, try adding a blazer on top of it.

I recommend opting for a thicker blazer to ensure you’re adding an extra layer of warmth. Also tie a scarf around your neck and slip on a pair of thermal leggings or tights.

Image source here

5) Pair with a long coat

With this option, you could either layer your dress with a sweater first or slip the coat on top of your dress if it’s a warm one. If your dress is shorter, you can always opt for tall boots. Don’t forget the thermal leggings!

Image source here

I hope you have gotten some great ideas or styling your maxi dresses in the winter. Remember, what’s most important is to have a good base and then build from there. Let me know which of these was your favorite look.

Do check out my post: 7 shoes to wear with dresses in the winter for more winter outfit inspiration.

I also have a post titled 5 ways to wear a pencil skirt in the winter in case you need some tips on styling yours outside of the summer months.

For those looking to wear maxi skirts all year-round, check out my post: The 8 Best Shoes to Wear With a Maxi Dress.

Until the next post,



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