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5 Innovative Ways to Wear a Maxi Dress in Winter

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It’s entirely possible to wear a maxi dress in winter and I’m showing 5 different ideas about changing out the layers and the footwear.

Quote of the day: “In the gym, if you experience no stimulus your muscles won’t grow. If you step under 10,000 pounds your body will break. Life is similar. Too much challenge makes life hard, but so does too little.” James Clear

The 5 Ways to Wear a Maxi Dress in Winter
1-Jacket & Ankle Boots
2-Sweater & Tall Boots
3-Long Sleeve Blouse & Closed-toe Shoes
4-Cardigan UNDER the dress & Tights
5-Turtleneck & Combat Boots

Even though most of us think of this item for the warm summer days, it’s also smart to be able to wear a maxi dress in winter too.
I took 2 different maxi dresses and worked my magic with layering and even talking about which footwear to include. Many of us live in more temperate climates, so there’s something for everyone here.

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Ways to Wear a Maxi Dress in Winter By Layering Over It

I think this is the layering option that is most popular with a summer item. Throw a layer over the piece and you’re good to go. There are way more than 2 ways of layering over the maxi dress:
1-Wear a vest
2-A shacket or any button-up shirt can be worn over it
3-You could wear a lighter-weight top and the maxi will look like a skirt. (very similar to #2 outfit photos below)
4-Any cardigan both long or short is a great layer
5-And the two options below

Related post: How to accessorize a print maxi

1-Jacket & Ankle Boots

Wear a maxi dress in winter with a jacket and ankle boots
Dress: Banana Republic ~~ Jacket: Peach c/o~~ Boots: Not Rated~~ Necklace: Alison + Aubrey c/o ~~Glasses: Glasses Shop

Any type of jacket can be worn over a maxi dress to make it work for the winter weather. If you live where it doesn’t get as cold, then a lightweight denim jacket or moto jacket is ideal.
For those with more frigid temperatures, you might pull out the fleece jackets, faux fur jackets, or even heavy leather jackets.

For the footwear, I chose ankle boots to give a little more coverage.


This faux suede jacket is from Peach when I was working with the company. The company has now gone of our business, but a jacket like this will be good for many years.

I did match the ankle boots to the color of my jacket and even used my eyeglasses as a way to continue the teal and browns throughout the outfit.

2-Sweater & Tall Boots

Tall boots and a sweater over top
Dress: G by Giuliana-thrifted~~ Sweater: Sundance-thrifted~~ Boots: no label- thrifted ~~Hat: thrifted

Even though you are wearing a maxi dress, that doesn’t mean you have to show off the entire dress. That’s the idea of layering an over-the-head sweater over your dress. My example here is showing a short sleeve sweater so you can see the sleeves of the maxi, but you can do this with ANY of your sweaters (or try it with a top).

I wore taller boots with this look to give the legs more coverage. These boots I would classify as mid-calf but you could wear knee-high boots or even over-the-knee boots. Again, I matched the boots to the sweater and even added a hat.


You don’t see many long-sleeved maxi dresses, so I snapped this up when I was thrifting recently.

Insider tip: If you find a long-sleeve item, but would rather it be short sleeve or sleeveless, most of the time it is easy to remove the sleeves. I did this with a shirt (shown here on Instagram) because the sleeves always were so wrinkled.

Ways to Wear a Maxi Dress in Winter By Layering Under It

I always try to remind myself that layering works both over a piece and under it too. So the next examples are all ideas to wear your maxi dress with layers beneath it. While I showcased three versions, don’t think you are limited by what I’ve shown here. Make sure to go through your closet and get innovative with your own wardrobe.

Here are a couple of examples you might have stashed in other drawers and places that could still be appropriate:
1- Some of your pajama tops might be the right piece
2-Workout tops or jackets
3-You partner’s items (just like I wore my husband’s shirt under an overall jumper here).
4-Or a casual sweatshirt

3-Long Sleeve Blouse & Closed-toe Shoes

Closed toe shoes and a long sleeve blouse
Dress: Banana Republic ~~ Top: Target~~ Shoes: Walking Cradles “Wyatt” c/o~~ Belt: Garnet Hill~~ Earrings: Theresa Rose Designs (found on Etsy)

If your maxi dress is sleeveless, this is a perfect opportunity to layer a statement-sleeve top under it. I’ve worn this ruffle blouse in multiple outfits including an edgy look and even super casual. There are ruffles on the bodice of the blouse also, but they get hidden with the maxi dress top.

Insider tip: Layering like this could be a great idea if you have a top that seems a tad tight. That part will be hidden under the top of the dress.

The shoe choice was a closed-toe shoe. If it’s still warm enough for bare legs, any kind of loafer, sneaker, or flat would work.


To break up the large expanse of blue from the maxi dress, I added a black and white belt. I carried the same color scheme into my shoes and earrings.
These loafers are from Walking Cradles. Just search for the shoes called “Wyatt“. The three of us recently reviewed three different styles of loafers and if you like classic shoes, you’ll love all of them.

The belt end is long, so I knotted it to keep it in place. Another trick is to use those handy-dandy clear elastics (found on Amazon here), as I’ve shown in this short video on Instagram.

4-Cardigan UNDER the dress & Tights

Tights and a cardigan for ways to wear a maxi dress in winter
Dress: Banana Republic~~ Cardigan: de Loux-vintage~~ Shoes: Steve Madden-thrifted~~ Necklaces: Loft and BaubleBar ~~ Tights: fleece-lined

Yes, I’m wearing a cardigan however, I buttoned it up and put it on under the maxi dress. Remember that a cardigan sweater with buttons could be worn as a normal sweater.

Insider tip: If the buttons tend to gape when you button them, try turning the sweater around and wearing it backward. Of course, you want to button the buttons first and then put the sweater over your head. We wore cardigans this way in the past here.

Just like with any skirt during the winter months, wearing tights can be the accessory of choice (especially the fleece-lined variety). Since I had matching fleece-lined tights in the same color as the maxi dress, I put them on. I also think a contrasting color would add a ton of fun to the look.

Insider tip: If you don’t like tights, then you can just as easily wear leggings or skinny jeans too.


This grey cardigan is very vintage. In fact, it used to be my mother’s when she was in college. That’s how vintage it is. You can tell I’m not lying because I just noticed that the elbow in the photo is thin. I’ll have to do something about that.

I wanted to show off the tights so I wore a pair of flats. These camo shoes were thrifted and are basically a Rothy’s dupe. The three of us reviewed another company that makes shoes out of recycled plastic bottles.

Insider tip: If you aren’t sure about secondhand footwear, I wrote an entire post about the process and how to clean them.

For this outfit, I layered 2 necklaces to add some shine to the look and add a vertical element.

5-Turtleneck & Combat Boots

Turtleneck and combat boots: Wear a maxi dress in winter
Dress: Banana Republic ~~ Turtleneck: Liz Claiborne-preloved~~ Boots: Rocket Dog~~ Necklace: Charming Charlies

Turtlenecks are the top of choice when it cools down, and are perfect for layering under your maxi dress for the winter.

For a different kind of boot to wear with a winterized maxi dress, I chose these floral combat boots. Combat and lug sole boots are very trendy right now, and the best part is they can work for women of any age. They add a bit of masculinity and edginess to a look.

Insider tip: I showcased 5 different clothing items with these boots last year, and a different maxi dress was even one of the options.


While I added neutrals with this teal maxi dress in the other examples, I wanted to showcase a brighter color here. The colorful boots and bright necklace and earrings give it an intentional look.
The multi-layered necklace came this way, but that doesn’t mean it can’t be layered with other necklaces. I’ve showcased it with 2 other necklaces here.

A Word About Maxi Dresses/Skirts

You may notice that both of my maxi skirts have a slit in them. This helps showcase a little leg so the bottom portion doesn’t seem as overwhelming. It’s also VERY helpful for being able to move and walk easier in it.

However, if that’s a detail that you don’t appreciate, there are maxi dresses and skirts that don’t have them. Another idea is you could sew it shut if the material has enough stretch. You want to make sure you can walk in it, haha!! Of course, you could always sew it just halfway shut too.

I didn’t show any options for tying up the ends of the maxi (like we have shown here) since the idea was to be more covered in the colder weather. But don’t forget, it’s an option too!

Options of wearing a maxi dress in the colder months

Photo credit: Rob Filogomo

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