Pumpkin spice season is officially here! (Insert my happy dance). Give me all the sweaters, jeans, booties, coats and hats. There are so many fall fashion pieces I love to wear. But one thing I wear throughout the year is a maxi skirt. They’re perfect to wear during the cooler months because maxi skirts offer more leg coverage compared to mini skirts that hit above the knee. 

A maxi skirt is a versatile piece that can be dressed up or down and doesn’t require tights because the skirt hits at the ankle. I mean, if I can get away with not wearing tights the entire fall and winter season that’s winning.

Because we’re getting into the cooler months of the year, I want to share how to wear maxi skirts in the fall. 

How to Wear Maxi Skirts in the Fall

maxi skirt with a moto jacket
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I rounded up some of my favorite maxi skirts for women. They’re perfect pieces to wear throughout the fall and winter.

Pair Your Maxi Skirt with an Oversized Sweater

Wear an oversized sweater with your maxi skirt or maxi dress for extra warmth. Because the sweater and the maxi skirt both are loose-fitting pieces, it’s best to break up the skirt and sweater with a skinny belt. You can add something like this Gucci belt to your natural waistline. This helps define your waist and gives you a more polished look. Tip: gather the extra material of the sweater in the back when you belt it, so the front lays nicely.

If you’d rather not wear a belt, you can also front-tuck the sweater into the skirt. I find that thinner sweaters look best when you front-tuck them into a skirt. 

maxi skirt with oversized sweater
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If You’re Petite, Here’s What You Can Do 

If you’re more on the petite side, you’ve probably found that a lot of maxi skirts/dresses are too long for you. Don’t count them out altogether from your wardrobe. You can search for skirts with a high-low hemline. Just make sure you know how long the back is, so it’s not dragging the ground. 

Look for retailers that provide varying lengths of skirts, like petite, regular, and tall. Abercrombie & Fitch sells varying lengths of their skirts, jeans, etc. 

See if retailers include measurements in their online descriptions of each piece. That way you know for sure if the maxi skirt or dress will be too long or not. 

If you have a t-shirt maxi dress, you can tie a knot on the side to bring the hemline up a bit. Pair the dress with some sneakers and a hat for an effortlessly casual look. 

Wear Boots or Sneakers with Your Maxi Skirt Outfits

For those particularly cold days, wear knee-high boots underneath your skirt for another layer of warmth. This can take the place of wearing tights, or you can wear comfy fleece leggings instead. No one will ever know they’re there with a maxi skirt.

Sneakers are another great shoe to pair with more casual outfits. During the fall, sneakers can take the place of casual sandals that you’d typically wear in the warmer months of the year. 

oversized sweater over a maxi dress
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Pair a Blazer or Denim Jacket for an Extra Layer

Layering pieces to create an outfit is one of my favorite things about fall fashion. Adding a blazer or a denim jacket is an easy way to add warmth to your look and still be on-trend. 

The oversized denim jacket is a trendy piece this season. Pair the maxi skirt with a denim jacket for more casual looks that include graphic tees, bodysuits, or turtlenecks

If you’re wearing your long skirt to the office, pair it with a blazer. Just make sure your skirt is a solid color and not too busy when paired with a patterned blazer, like a plaid or houndstooth.

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Fall Maxi Skirt Outfits

There are so many different maxi skirt outfits you can put together from super casual to belle-of-the-ball formal. And I bet you have most if not all, the pieces already in your closet to pair with a maxi skirt. Some tops to wear with maxi skirts include graphic tees, cropped sweaters, cardigans, oversized sweaters, and bodysuits to name a few. Below I rounded up some cute maxi skirt outfits.

Maxi Skirt with Cropped Sweater

The below-cropped cardigan is sold out right now, but I found this cropped sweater instead. It’s the perfect top to pair with a maxi skirt – especially a slip skirt. It will hit right at the top of the skirt, so you don’t have to worry about tucking it in. Finish the look with booties or knee-high boots. I prefer to pair knee-high boots with skirts this length, so it lengthens the look of my legs.

Sometimes booties can cut the look, depending on the height of the bootie. If you’re going to wear a bootie, I’d recommend a low-profile option that has cut-outs on the sides.

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Maxi Skirt with a Graphic Tee

For a street-style look, pair a maxi skirt with your favorite graphic tee and sneakers. A solid-colored skirt looks best with busier tees. Finish the outfit with a hat and crossbody bag for the perfect look to go to your next concert.

I just paired a basic white tee with this skirt and knotted the bottom of the shirt for more of a cropped fit. You can do the same with true graphic tees or a button-down shirt.

pleated skirt with a tee
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A Tiered or Pleated Maxi Skirt with a Blazer

The next two outfit ideas options are examples of how to wear a maxi skirt in the fall for work. If you’re wearing a skirt to the office or a more dressy occasion, opt for skirts that have feminine details like a pleated maxi skirt or ones with lace or tiers. A maxi skirt is a great staple piece for the office. It’s stylish and sophisticated, yet they’re typically super comfy. Throw on a blazer and a poplin shirt with a little ruffle detail for the perfect workwear outfit during the fall. 

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Maxi Skirt with a Lace Top

A maxi skirt with a long-sleeved lace top is a fun and sophisticated look to wear to the office or on your next date night. A sweater skirt is so comfortable if you’re sitting at a desk most of the day. I prefer them to trousers any day. The texture elements of this sweater maxi skirt with a slit paired with the lace top give the look interest. Finish the look with my favorite pair of pumps.  

maxi sweater skirt with lace top
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Maxi Skirt with a Denim Jacket

A denim jacket doesn’t have to look casual. Look for interesting details like a puff sleeve on a denim jacket to dress up the overall look. Pair a slip skirt with a bodysuit and a fun sandal or knee-high boot (depending on the weather) with the denim jacket. It’s the perfect outfit for lunch or brunch.

maxi skirt with a denim jacket
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If you don’t have a maxi skirt, I hope this inspires you to add one to your wardrobe and gives you plenty of ideas on how to style it!

What’s your favorite way to wear a maxi skirt? Let me know in the comments below!



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