The Return of the Maxi Skirt Winter Outfits: Tips

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Look your best this winter season with these trendy maxi skirt winter outfits! Maxi skirts have made a huge comeback over the last year. And while they’ve been a staple for many spring and summer outfits, maxi skirts are also a good option for winter. However, you’ll need to pair them with the right pieces to create a warm and cozy outfit for the colder months.

But many women have a hard time styling maxi skirts for cold weather. That’s because it can be challenging to find the right shoes or tops that don’t add unnecessary bulk. If you’re looking for inspiration on how to style maxi skirts for winter, you’re in the right place. Here are our go-to looks for the best maxi skirt winter outfits.

The Best Maxi Skirt Winter Outfits

Pleated Skirt with Oversized Jacket

This is one of our favorite looks for winter. It all starts with a pleated maxi skirt, which adds texture and movement. Having the fuller skirt gives more room in the hips, so it’s not as constricting as other styles. To combat that flowy look, we’ll be pairing the maxi with an oversized jacket. We recommend looking for one that has a boxy structured look, as it provides balance to the outfit. 

We recommend that you stick with a neutral color for either the skirt or jacket. Then the other pieces can be colorful or patterned for a brighter, more eye-catching aesthetic. Layering is also important, but you have lots of options for what to wear underneath. A graphic tee or fitted tank is perfect for offsetting the loose look created by the skirt and jacket.

Complete the look with a chunky knit scarf or beanie, especially if it’s an extra cold day outside. And if you want to make this look a bit edgier, a good old fashioned pair of combat boots will do the trick!

Flared Skirt with Cropped Sweater

When it comes to effortless sophistication, you can’t go wrong with a flared skirt and cropped sweater. This creates a flattering silhouette that looks stunning on practically every body size and shape. That’s because the volume of the long maxi is balanced by the sweater, which accentuates the waistline. 

Ideally, your flared skirt should hit right above the ankles. You’ll also want to make sure it has a high-waist as to not expose your belly to the chill of winter! For the sweater, don’t be afraid to play with different materials and textures. For example, a sweater that is knitted and ribbed will give your look a cozy and relaxed winter look.

For your footwear, a pair of heeled ankle boots or knee-high boots will elevate the outfit. It also adds another layer (which is crucial for winter!) to ensure you’re staying warm! However, a pair of sneakers can downplay the look to give it more of a sporty feel. As long as you have a warm pair of socks, you should be fine tackling the winter!

pleated maxi skirt winter outfits
Mango
maxi skirt winter outfits sweater
Lulus

Slim Maxi Skirt with Cardigan

If you want a stylish look you can wear to work or to a formal event, pair a slim maxi skirt with a fitted cardigan. With the sleek profile of the skirt, you’ll exude a professional and polished appearance that’s sophisticated but trendy.

A black or dark-colored skirt is best, although you can find ones with interesting elements like slits and asymmetrical waistbands. Having that neutral base also makes it easier to have something brighter on top. This could be a colored V-neck cardigan or even something with a playful pattern! The best way to style the sweater is to button it halfway or all the way to the top. You don’t want to keep it open, as the loose fabric can be unfitting and unflattering on some body shapes.

If you prefer a more refined look, this combo is stunning with heeled ankle boots. But if you want to make it more casual, a pair of loafers or flat knee-high boots also works well.

maxi skirt winter outfits black skirt
Free People

Denim Maxi Skirt with Boots

Denim maxis were all the rage in summer. But just because the temperatures have dropped doesn’t mean you have to retire them for the season. With the right pieces, you can turn your denim skirt into a stylish and comfortable number that’s perfect for winter!

The key thing to consider when styling your denim maxi is your footwear. While you may have worn sandals or sneakers when it was warm, it’s better to bring out your favorite pair of winter boots. To recreate the look we’ve seen all over Instagram, we recommend a pair of below-the-knee leather boots. This will keep your feet warm while also adding dimension to the denim.

These types of boots look best when you have a denim skirt with a slit. Not only does a slit give you more movement, but it also draws your eye to highlight your footwear. 

When it comes to accessories, you also have a lot of options. Having belt loops on your denim maxi means you can add a contrasting leather belt. Choose one in the same color of your handbag for a cohesive look that looks fresh off the runway!

Stuart Weitzman
denim maxi skirt winter outfits
Bloomingdale's

Add to Your Wardrobe Essentials

As you can see, there are tons of adorable maxi skirt winter outfits to wear this season. With the right sweaters, boots, and accessories, you can still look stylish while staying warm in the cold weather. For this reason, a maxi skirt is one of our winter capsule wardrobe essentials everyone should invest in. Whether you’re curating a casual daytime outfit or shooting for something more refined and polished, a maxi skirt is a versatile item. The key is to mix textures, silhouettes, and winter-appropriate accessories for a balanced look that shines!

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