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Weeks after Copenhagen Fashion Week 2025, I'm still feeling inspired by all the street style looks from the event. Most recently, they prompted me to take a long hard look at my closet and debate what to wear with a pleated skirt. It seemed like every notable It-Girl and stylish attendee I saw was wearing short, midi, and maxi pleated skirt outfits with those signature vertical folds. And then Anne Hathaway showed up on the set of The Devil Wears Prada sequel in one (as seen above), all but confirming this will become fall's favorite piece.
In fashion, almost every trend is connected to another through an invisible string. Pleated skirts are no exception. The fact that they're trendy again can be traced back to all those cute tennis skirts we’ve been seeing on every notable runway show (think Miu Miu, Tommy Hilfiger, and Burberry) from the past year. As a result, the popularity of “tenniscore” and “prepcore” is branching out even further into pleats of all kinds and styled to match every mood.
Which is why I didn't have to stand in front of my closet for too long wondering how to wear a pleated skirt. I instantly found a top, a blazer, and shoes that seamlessly worked with a pleated midi I bought from Aritzia more than a year ago. In fact, I perhaps had a little too much fun playing dress up in front of my mirror because I soon discovered that there are actually endless ways to style the preppy skirt.
Rather than send you my awkward selfies, I’ve collected all the best outfit ideas and styling tips, below. Here's how to style a pleated skirt for fall 2025 like the fashion pros.
With a Pullover and Sneakers
For a pleated skirt look that leans into the preppy aesthetic, pair a cozy knit, long socks, and comfortable sneakers with a mini or midi skirt. A collared pastel or white button down layered beneath the crewneck adds a final touch that takes the outfit from relaxed to polished.
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With a Blazer and Boots
The cooler temperatures are fast approaching, which means it’s time to grab out that oversized blazer and boots again for an office or date night look. Opt for a longer skirt, like the pleated midi skirt seen here, that can fully cover the tops of your boots. A matching vest underneath the blazer is also a chic choice; if you don't have one, then a simple cardigan or tank top works too.
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With a Button Down and High Heels
Styling a pleated skirt doesn’t require buying a ton of new items. If you want to keep it simple, yet striking, then a short sleeve button-down shirt and everyday pumps can go a long way. The boxy fit of the shirt pictured here on Tracee Ellis Ross feels extra chic, but you can just as easily take any white button-down and style it to your liking (like adding tights once the weather gets cold). Wear this look to your office for a comfortable but compliment-inducing look.
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With a Sculptural Blazer
Oversized this, oversized that…but what’s really trending in 2025 are artistic, sculptural blazers. The smart ensemble makes a powerful and beautifully feminine statement. Style with a high waisted midi skirt and a pair of black pumps to recreate that iconic Dior The New Look.
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With a Cardigan and Loafers
Draping a cardigan over your shoulders like your high-school history teacher did is on trend again, and it happens to look great over a pleated skirt. To stick to the preppy theme, opt for high socks or tights and your go-to loafers. These are all pieces you likely already own in your closet, but just in case, here are some cute ones to consider:
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With a Polo Shirt
Further proof that there are so many different ways to style pleated skirts: I’ve bought a number of polo shirts and sweaters in the past year, and they all go well with the versatile bottom. That’s because like calls to like, and the combo completes one cohesive aesthetic fit for a courtside tennis match. I chose skirt with box pleats to give the ensemble a more sophisticated appeal. Again, a cardigan is a good layering option once the weather gets chilly.
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With a Hoodie and Leather Jacket
No fall wardrobe is complete without a leather jacket. This year, we’re moving away from the fitted leather looks and returning to the boxy, borrowed-from-the-boys silhouette. Keep it extra casual (and supremely snuggly) with a hoodie underneath. Slip into a pair of white sneakers to finish the outfit.
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SoComfy Full-Zip Hoodie Sweatshirt
With a Long Trench Coat
Another fall essential is the trusty trench coat. Wear it over a mini or maxi skirt, and let its long train drape over your ensemble (and keep you warm). A T-shirt creates a playful contrast of casual and sophistication. But for a more polished appearance, you could style with loafers, ankle boots, or knee-high boots and accessorize with classic earrings and sunglasses.
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With a Silk Scarf Tied Around the Waist
The unexpected breakout star of 2025? Silk scarves and all the unique ways you can style them. Right now, tying one around your waist is the go-to for fashion pros (as pictured here) and has more versatility than you’d think. The stylish accessory pairs wonderfully with some pleats, too. And while summers may have called for ballerina flats, fall outfits require your trusty tall boots and a long sleeve blouse or turtleneck.
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With a Trendy Top and Shoes
A pleated a-line skirt is peak simplicity, but styled with trend pieces like slim sneakers and a striped top, the vibe is just the right amount of cool. The look leans more casual, making it perfect for a brunch date, or for wearing on the weekends. While I would personally go for a monochromatic ensemble, colorful combos work too. A denim jacket works as an extra layer for this casual look as well.
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