How to Wear Maxi Dress in Winter

Two women wearing maxi dresses reading on a cold winter day
Are you wondering how to wear maxi dress in winter? It's tricky but it's not impossible. Learn how to keep yourself warm and stylish.

You know what I loathe most about winter, besides the freezing temperature? The fashion. Everything people wear, from knitted dresses to winter jackets, is heavy, dark, and dreary. It’s no wonder the entire season feels so emotionally low.

But what if I told you winter doesn’t have to feel like a three-month-long mourning period? What if we could repurpose our bright, sunny, and fun maxi dresses with pockets and bring a burst of color to an otherwise gloomy period.

You see, maxi dresses are long and breezy, which means they offer more coverage for your torso than those dreary sweater dresses. And because they are long, you can wear thermal leggings, pants, and even boots underneath without ruining the style. If you learn how to layer the dress for some warmth, it can become even more eye-catching than it was during summer.

This, however, is easier said than done. Repurposing a maxi dress for winter requires more creativity than just throwing on some slippers and shades. Luckily, we’ve got all the tricks you’ll need to pull off more than five looks and look stylish all winter long.

But first…

Tips to Make Maxi Dress Work for Winter

Be practical

Although buying a maxi dress during winter is a fantastic idea, you have to consider the practicality of doing it. After all, you don’t want to drag the dress through three feet of snow. However, if there’s only a light dusting of snow or none at all, you can don your maxi dress comfortably. This applies too if you are planning to stay indoors.

Mind the Materials

Some fabrics are better suited for the winter than others. Wintery fabrics should be a bit heavy. I personally prefer breathable fabrics such as different types of cotton; But synthetics unbeatable fabrics can work in the winter as well, not letting the warmth out.

Among the best wintery fabrics there are:

  • Cotton
  • Cotton Jersey
  • Fleece
  • Wool
  • Velvet

Layer up

The only way to winterize an otherwise light and summery dress is to layer it up with other warm clothing. Think of a turtle neck or long sleeve tee inside and jackets or coats on top. I love my maxi dresses with pockets because I can always sneak my hands inside the pockets for that extra warmth.

Cover the Legs

The dress may be covering your legs all the way to the ankles, but your feet will probably still freeze. Add some layers on the bottom part too by donning some leggings, tights, and even pants if the style allows. Boots and sneakers are also appropriate to ensure your feet are nice and toasty.


Just because it’s winter and you are all layered up doesn’t mean you have to look any less of a lady. On the contrary, winter allows even more accessorizing with scarfs, hats, and gloves. Feel free to also wear huge hoop earrings so they can pop.

different styles of wearing maxi dresses during the winter

Maxi Dress in Winter Ideas

1. Make It Cozy

I’ve made this the first option because many people want to be warm and snug throughout those cold months. For this look, choose a straight, warm maxi dress that accentuates your curves and makes you look tall. You can also wear a long sleeve tee inside or a turtle neck to maximize the warmth.

You will wear a faux fur teddy coat to bring more coziness and warmth into the outfit, and don some tights for layering. Finish the look with a warm winter hat, some ankle-length boots, and hoop earrings to bring everything together. Some cotton gloves won’t hurt either.

2. The Edgy Look

For this look, you will maintain the straight maxi dress, long sleeve tee inside, and stockings for warmth. Instead of a winter coat, however, you will pair the look with a vegan leather jacket and knee-length leather boots. Take the edge all the way up with some leather gloves as well and a mini backpack.

However, you can make this look a bit more relaxed by wearing white sneakers instead of leather boots. Take your hair down to cover the ears, or wear a winter fedora if it’s too cold.

3. The Shirt Dress

One thing about maxi dresses is that they come in different designs. Shirt dresses or buttoned-down maxi dresses are the ultimate layer piece during winter because they are easy to style. You can wear the dress buttoned, half-buttoned, or completely open like a coat.

With a turtle neck underneath and some leather leggings, you can wear the dress unbuttoned from the waist down. This look also goes amazingly well with a pair of cropped jeans (any straight pants will do) and ankle boots if you want to look sexy. For outerwear, throw on a long classic trench coat to bring everything together.

You can accessorize this look with a belt, a small leather handbag, and bracelets on your hands.

4. Maxi Dress with Pockets

Speaking of versatile dresses, nothing works better for winter than a maxi dress with pockets. Instead of wearing gloves or long-pocketed coats, you can just put your hands in the dress pockets for some warmth. These pockets also come in handy when you want a casual look without carrying a purse.

So, how does one pull it off in a stylish way? The secret is to layer it up with a turtle neck, cropped jacket, and a scarf. If you are feeling casual, throw on some light sneakers. The look also works well for office wear if you replace the jacket with an official blazer and more work-appropriate boots. Finally, you can opt for long underwear instead of leggings to keep the style minimal.

5. The Holiday Look

The holiday look is appropriate for all those parties you will attend during the festive season and any celebratory event. For this look, don a sequin maxi dress that screams party in every sense. You can wear a plain tee inside and a plaid coat on top. The two add warmth to your body without breaking the style.

Accessory-wise, go with black closed heels and a clutch. You can choose to wear leggings or not depending on how cold it is but make sure it doesn’t look bad. Gold earrings and a swipe of your favorite lipstick will bring this perfect holiday ensemble together.

6. The Serious Look

Sometimes you want to go to important places such as a job interview. In these cases where winter coats and leather jackets will be inappropriate. In this case, wear a blazer on top of the maxi dress. Choose bright-colored coats like white or beige to make the look less wintery. You can finish off the look with a classic scarf and popping earrings. I always like to make sure my dress has pockets, so it’s easier to store simple things like lip balm and my phone. This way, I don’t have to carry my bag with me.

7. Be Relaxed

Yes, you can have a relaxed look even in winter, especially if it’s not snowing. Instead of coats and jackets, put a turtle neck or tee underneath the dress and layer it with a chunky sweater. This look doesn’t require any leg wear, so you will just throw on some sneakers, and a bracelet, and you are out of the door. It is the perfect look for the weeks ahead of spring because you will look relaxed and fun.

Can I wear a maxi dress in the winter?

Of course you can. As long as the way you wear it keeps you warm with the right combination between layers and the dress’s fabric – maxi dresses are a great outfit for the winter.

Lior Shapiro

I love clothes with pockets and dresses, and I think any woman can pull off a good maxi dress.
I believe women's clothes with pockets make the world a better place.