What To Wear With Maxi Skirts For Cooler Weather

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As the seasons change, mini skirts take a backseat to longer hemlines.

Mini skirts are great and can be worn for the transitional seasons, but nothing beats a maxi skirt to grab someone’s attention. 

As we transition our wardrobes to fully embrace the cooler season, there are a few reasons why maxi skirts in all silhouettes and fabrics reign supreme.

Regardless of personal style, they’re seasonless, versatile, and a closet staple for the office or casual affairs.  The versatility of the ankle-grazing skirt allows it to easily transition from a brunch look with friends to an office-appropriate staple.  

What to Wear with Maxi Skirts

For a laid-back off-duty model look, pair the closet staple with a blazer or leather jacket and knee-high boots for a casual fall weather look. Don’t forget a statement bag to add extra elegance to the casual look.  

Whether it be a denim maxi skirt or a column skirt, any of those choices work regardless of body shape or body type. 

Scroll below for inspo on what to wear with maxi skirts for the cooler seasons. 

1. Button Down

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Instagram @valerie.kei

Covering half of your body with fabric, may seem overwhelming for many, but it doesn’t have to be.

The ultimate way to style a column skirt is with a button-down shirt with the sleeves rolled up and matching ankle boots.  Certainly, there’s something in the way a maxi moves that’s endlessly appealing.

All that fabric flows so pleasingly around the ankles, creating its own drama as the wearer strides by a maxi skirt. 

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Instagram @gabriellazacche

Swapping in a denim maxi is a great substitution for straight leg jeans to look more put together with minimal effort.

Denim maxis offer endless styling opportunities throughout the year, including a denim white maxi skirt. A longer hemline can be a great foil to plunging necklines, whether it be with a blouse or cropped top for warmer months. 

Finish off with ballet flats or sneakers for a relaxed vibe. 

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Instagram @ingridedvinsen


A versatile piece, the column skirt will be a forever favorite.  

This classic silhouette fits snug through the hips and straight throughout the body.

Pair it with an unbuttoned blouse and on-trend brown kitten heels for a chic fall vibe. 

2. Cardigan/Sweaters

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Thanks to lightweight fabrics and breezy silhouettes, a maxi skirt look can be as comfy to wear as their shorter counterparts.

Whether you’re pairing yours with a tank top or an oversized cardigan, you can rely on the floor-sweeping skirt.

Finish off with comfortable flats or sandals to ground the flowy boho style skirt. 

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Instagram @peggy_loves

It is easy to elevate the humble sweater with utter sophistication. Keep the trending look feeling extra polished by pairing it with a maxi skirt length.

When inclement weather strikes, simply style with chunky boots, or even cowboy boots, if you are feeling adventurous. 

3. Blazers/Jackets

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Instagram @viaemmajang


Turn to blazers for an instant sartorial success.

Take the guesswork out of getting ready, and reach for a black blazer or any solid color blazer for timeless elegance.

A long denim skirt is the perfect balance between the tailored blazer and the casual skirt. 

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Instagram @lovisabarkman

The satin skirt exudes a vibe that is elegant and regal. Choosing a maxi satin skirt in fall colors of brown, navy, or olive is even better.

Elevated basics are the easy go-to picks to style with a slip skirt for the cooler season.

For special occasions or even casual outings, opt for an oversized blazer and chic slingbacks. 

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Instagram @nlmarilyn


For an effortless maxi skirt outfit, turn to a black maxi skirt. 

They look incredibly chic with just about anything! During those early autumn days, a simple white t-shirt and strappy heels will be your date night look. 

Add a light jacket and trendy flats for a unique style that will certainly turn heads. 

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Instagram @lolariostyle

A great denim shirt, or even a denim jacket is essentially a neutral piece. It is a true wardrobe classic and a workhorse.

Wearing all of your best wardrobe essentials at once is a no-fail solution for easy, elevated style. 

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It’s no secret that the leather jacket is the unsung hero of any transitional capsule wardrobe.

Built to withstand any element, a versatile black biker leather jacket is the ultimate trans-seasonal and wardrobe staple.

Pair it with a satin skirt for the ultimate contrast of edgy and feminine pieces.