How to Style Pleated Skirts in 2026?

How to style a pleated skirt in 2026? Surely it depends on the length of the skirt. Whether you opt for a short or midi length, the pleated skirt offers a touch of boujee to any outfit. From preppy to office-ready, the pleated skirt is a wardrobe favourite that deserves a place in your closet. Scroll down to see the best pleated skirt outfits 2026 for every age.

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Key Takeaways

  • Explore pleated skirt outfits 2026 for every occasion, from casual to office-ready.
  • Find various styling tips such as pairing pleated skirts with blouses, t-shirts, and sweaters.
  • Discover the versatility of the pleated skirt for different seasons, including winter and summer looks.
  • Learn how to transition pleated skirt outfits from day to night effortlessly.
  • Sign up for updates on new pleated skirt trends and styling ideas through Brunette from Wall Street Substack.

HOW TO STYLE A PLEATED SKIRT IN 2026

As always, all the collages in this article are hyperlinked and available for immediate purchase. You can shop for all the pleated skirt outfits (short pleated skirt outfits and midi pleated skirt outfits) presented in this article as you read. To shop for the pleated skirt outfits presented, simply click on the item you want to buy. One simple click will take you to the store (I only link to the stores I shop from and know they are trustworthy) where you can purchase that item.

*We are adding new pleated skirt outfits 2026 constantly – make sure you subscribe to Brunette from Wall Street Substack to make sure you don’t miss a new pleated skirt outfit. Also, become a paid Brunette from Wall Street Substack subscriber if you want to leave a comment, ask a question, or find out why we style a pleated skirt with that top and those shoes.

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1 PLEATED SKIRT OUTFITS WITH A BLOUSE

RED SHORT PLEATED SKIRT WITH RED RUFFLE SILK BLOUSE AND BLACK MID HEEL SLINGBACK PUMPS

PINK MIDI PLEATED SKIRT WITH SHORT SLEEVE ORANGE PINK BOW BLOUSE AND SANDALS

PINK MIDI PLEATED SKIRT WITH SHORT SLEEVE ORANGE PINK BOW BLOUSE AND BLACK KITTEN HEEL SLINGBACK PUMPS

PINK PLEATED MIDI SKIRT WITH TRANSCENDENT PINK SILK BLOUSE AND HIGH HEEL MULES WITH OFF WHITE DOUBLE BREASTED WOOL COAT

RED MIDI PLEATED SKIRT WITH SHORT SLEEVE ORANGE PINK BOW BLOUSE AND BLACK SLINGBACK PUMPS

2 PLEATED SKIRT OUTFITS WITH A T-SHIRT

3 PLEATED SKIRT OUTFITS WITH A CROP TOP

4 PLEATED SKIRT OUTFITS WITH A SLIP TOP

MIDI NAVY BLUE PLEATED SKIRT WITH A SLIP TOP UNDER A WHITE DOUBLE BREASTED BLAZER AND HIGH HEEL PONITY MULES

5 PLEATED SKIRT OUTFITS WITH A SWEATER

BROWN BEIGE MIDI PLEATED SKIRT WITH CAMEL PONCHO CROPPED SWEATER AND POMEGRANATE BURGUNDY KITTEN HEEL SLINGBACK PUMPS

RED MIDI PLEATED SKIRT WITH NAVY BLUE SHORTSLEEVE CREWNECK SWEATER AND DENIM KITTEN HEEL SLINGBACK PUMPS WITH NAVY BRAIDED HEADBAND

RED MIDI PLEATED SKIRT WITH CHRISTMAS SWEATER AND POINTY PATENT LEATHER KITTEN HEEL SLINGBACK PUMPS

NAVY BLUE MIDI PLEATED SKIRT WITH CAMEL CABLE KNIT SWEATER UNDER A CAMEL TRENCH COAT AND BLUE SATIN PUMPS

6 PLEATED SKIRT OUTFITS WITH A CARDIGAN

RED MINI PLEATED SKIRT WITH LIGHT PINK CROPPED CARDIGAN SWEATER AND CHERRY LACQUER KITTEN HEEL SLINGBACKS

7 PLEATED SKIRT OUTFITS WITH A BLAZER

PINK LEATHER MIDI PLEATED SKIRT WITH PINK DOUBLE BREASTED BLAZER AND PINK PUMPS

RED MIDI PLEATED SKIRT WITH PINK DOUBLE BREASTED BLAZER AND BLACK MID HEEL PUMPS WITH CHERRY LACQUER BRAIDED HEADBAND

8 PLEATED SKIRT OUTFITS WITH A BOMBER JACKET

9 PLEATED SKIRT OUTFITS WITH A TWEED JACKET

AIRY BLUE MIDI PLEATED SKIRT WITH MATCHING AIRY BLUE BELTED TWEED JACKET AND BLUE HEADBAND WITH BLACK HIGH HEEL PUMPS

10 PLEATED SKIRT OUTFITS WITH A LEATHER JACKET

11 PLEATED SKIRT OUTFITS WITH A DENIM JACKET

NAVY BLUE MIDI PLEATED SKIRT WITH SHORT BLUE DENIM JACKET ON FLORAL BLOUSE WITH PINK STILETTO PUMPS

12 PLEATED SKIRT OUTFITS WITH A TRENCH COAT

13 PLEATED SKIRT OUTFITS WITH A WINTER COAT

14 PLEATED SKIRT OUTFITS WITH HEELS

15 PLEATED SKIRT OUTFITS WITH FLATS

16 PLEATED SKIRT OUTFITS WITH BOOTS

PINK MINI PLEATED SKIRT WITH WHITE KNEE HIGH BOOTS AND WHITE CABLE KNIT TURTLENECK SWEATER AND CHERRY CODED RED BRAIDED HEADBAND

RED SHORT PLEATED SKIRT WITH KNEE HIGH BOOTS AND LONG BLACK COAT ON A NAVY DOUBLE BREASTED BLAZER WITH A HEADBAND

17 PLEATED SKIRT OUTFITS WITH SNEAKERS

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