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The 21 Best Long Skirt Outfits for the Office and Beyond

The best long skirt outfits all have one thing in common: They're an opportunity to show off your layering abilities.

best long skirt outfits
Edward BerthelotGetty Images

Nobody has to work hard to convince anyone of the merits of the miniskirt: It's a '60s-era fashion staple that's hardly lost its luster. Longer iterations—midis, maxis, and everything in between—haven't enjoyed the same reputation, likely because they're not the easiest to wear. But the best long skirt outfits all have one thing in common: They're an opportunity to show off your layering abilities.

Even better, long skirts can be worn all year round—even in the sweltering summer—when styled creatively; take your cues from the street style on display below. While one fashion show-goer pairs a flowy, pleated midi skirt with a sporty black halter and ladylike flats that could work for any weekend plan, another dresses up a knit-rib maxi skirt with a matching sweater top for a coordinated look that's perfect for the office. For chilly weekend nights, don't be afraid to layer a long skirt with a cropped jacket for a play on proportions. Ahead, find the 21 best ways to wear a long skirt—plus, shop our favorite picks to get the look.

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Sporty Spice
a woman wears a long pleated skirt with a black top tucked in in a roundup of the best long skirt outfits 2022
Christian VierigGetty Images

Offset the femininity of a flowy midi skirt with a halter top.

Halterneck Tank Top
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Major Blazer
a woman wears a belted blazer over a long skirt in a roundup of the best long skirt outfits 2022
Edward BerthelotGetty Images

Secure an oversized blazer, layered over a patterned skirt, with a belt.

Taupe Gelso Blazer
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The Frankie Shop
Collar Up
a model wears a printed long skirt and a quilted top in a roundup of the best long skirt outfits 2022
Edward BerthelotGetty Images

Double up on collars for a long skirt outfit that's office appropriate.

Oversized Shirt
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Cool and Casual
a model wears a long silk skirt and a sweater in a roundup of long skirt outfits 2022
Jeremy MoellerGetty Images

A silk skirt is the perfect substitute for pants—especially when you pair it with your favorite sweater and comfy sneakers.

Phantom Low-Top Sneakers
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Mix Prints
a woman mixes two stripe prints including a long skirt in a roundup of the best long skirt outfits 2022
Christian VierigGetty Images

Take a note from Gabriella Karefa-Johnson and pair a striped skirt with a striped cardigan.

Multicolor Alpaca & Wool Stripe Soft Cardigan
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Dressed Down
a woman wears a white t shirt and long printed skirt in a roundup of the best long skirt outfits 2022
Claudio LaveniaGetty Images

A tee magically becomes meeting appropriate when paired with a colorful midi skirt and heels.

Relaxed-Cut T-Shirt
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Color Story
a woman wears a button down shirt and pink long skirt in a roundup of the best long skirt outfits 2022
Edward BerthelotGetty Images

Pair a colorful pink skirt with equally prim flats for a wear-anywhere outfit.

Maia Fabric Ballerina Flats
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The Slit Skirt
a woman wears a slit trench skirt and longline coat in a roundup of the best long skirt outfits 2022
StreetstyleshootersGetty Images

If a long skirt feels too stifling, try pairing one that features a high slit with a trench coat.

Cotton Gabardine Double-Breasted Trench Coat
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Color-Block It
a woman wears a purple t shirt and long yellow skirt in a roundup of the best long skirt outfits 2022
Christian VierigGetty Images

The easiest way to make a skirt that hits at the knee feel age appropriate? Pair it with a tee in a shade on the opposite side of the color wheel.

PPRMINT™ Organic Cotton T-shirt
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Get Creative
a woman wears a tucked in button down skirt and shirt in a roundup of the best long skirt outfits 2022
Edward BerthelotGetty Images

Looking to make a long skirt outfit more interesting? Tuck your shirt into the belt for some added visual appeal.

Everyday Cotton Long-Sleeve Shirt
The Frankie Shop
Top It Off
a woman wears a pleated long yellow skirt with a bucket hat to illustrate a roundup of the best long skirt outfits 2022
Daniel ZuchnikGetty Images

Make any outfit feel instantly cooler with a bucket hat.

Texture Bucket Hat
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Down-to-Earth Tones
a woman wears an all orange outfit with a moss green bag to illustrate a roundup of the best long skirt outfits 2022
Edward BerthelotGetty Images

Ground a voluminous, all-orange look with moss green accessories.

Marcie Small Saddle Bag
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Pleat with Me
model paloma elsesser wears a plaid skirt and a crop top to illustrate a roundup of the best long skirt outfits 2022
Melodie JengGetty Images

Keep a colorful pleated maxi from veering into costume territory with smart layering and accessories.

Horseshoe Leather Waist Belt
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Boots for Walking
a model wears a long skirt with an oversized sweater and knee high boots in a roundup of the best long skirt outfits 2022
Edward BerthelotGetty Images

The best way to make any skirt outfit all-weather appropriate is with knee-high boots. Choose a pair in a color similar to the skirt itself for an even more sophisticated vibe.

Meg Knee Boot
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Matchy-Matchy
a model wears a matching knit set with a skirt and ribbed top in a roundup of the best long skirt outfits 2022
Edward BerthelotGetty Images

Need more proof that matching sets aren't just for suits?

Rylan Knit Two Piece
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Layer Smart
a woman wears a trench coat and a wrap maxi skirt in a roundup of the best long skirt outfits 2022
StreetstyleshootersGetty Images

On cooler days, treat a long skirt as an extra layering piece by securing it over a long dress or jacket.

Bravery Trench Coat
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The Coolest Color Block
a woman wears a bright skirt and orange top in a roundup of the best long skirt outfits 2022
Daniel ZuchnikGetty Images

Make a skirt feel all the more playful by color-blocking it—with every other color.

Amber Shoulder Bag
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Crop It
a woman walks at fashion week wearing a fringe midi skirt in a roundup of the best long skirt outfits 2022
Christian VierigGetty Images

Looking to add some edge to your fringed midi skirt? A bra top-leather jacket combo is the easiest way to make it instantly less saccharine.

Waffle Bralette
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Net Neutrality
a woman stands in a street wearing a long shirt and a white button down in a roundup of the best long skirt outfits 2022
Edward BerthelotGetty Images

A beige maxi skirt looks perfectly chic with a simple white button-down.

Relaxed-Fit Crepe Shirt
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All Ears
best long skirt outfits
Christian VierigGetty Images

Finish off any outfit—skirt or otherwise—with attention-grabbing chandelier earrings.

Maxi Rainbow Pfefferminz Earrings
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Top It with a Shacket
best long skirt outfits
Edward BerthelotGetty Images

Make any skirt outfit an easy choice for a freezing office by pairing it with a shacket.

Kally Shirt Jacket
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