By Bryan Goh - published
The pleated skirt has spent decades being pressed into service, where it belonged to school uniforms, sensible work wardrobes and Queen Elizabeth II, who made it part of her unofficial off-duty uniform starting from the ’50s. None of this did much for its fashion reputation, though the skirt itself kept remarkably good form.
Today, its reputation has since been neatly pressed out. Brands have brought it back into the fold, like Dior, Partow and Rabanne, with their pre-fall 2026 collections, while Calvin Klein and Chanel picked up the line for fall/winter 2026, alongside Prada and Ermanno Scervino. It’s the kind of fail-proof piece that can be worked in a myriad of ways depending on the occasion: buttoned up with a sensible Oxford shirt for the office, or dressed up for date night with a plunging V-neck top.
A pressing issue, however, is proportion. Look for pleats that fall cleanly through the waist and hips, and consider the hem carefully. Knee-length versions can still skew school uniform, while a mid-calf is usually the more sophisticated cut.
Here, seven ways to style this fail-proof piece that can be worked in a myriad of ways, from sporty layers and oversized shirting to romantic ruffles and everything in between.
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1. With a Retro Jacket And Kitten Heels
When a pleated skirt is paired with a retro-looking sports jacket and kitten heels, the result is country club polish meets fashion-week eccentricity.
Pointed Crystal-Heel Slingback Pumps, $69.90, Charles & Keith
A little sparkle beneath all that sportiness keeps an outfit from taking itself too seriously.
Firebird Track Top Loose, $119, Adidas
Those signature stripes lend just enough athletic credibility to offset a pleated skirt’s ladylike leanings.
Cotton Poplin Midi Skirt, $420, Citizens of Humanity at MyTheresa
Crisp cotton poplin gives the pleated silhouette enough structure to hold its own against sporty separates.
2. With Tailoring and Unexpected Hardware
Pleated skirts naturally pair with tailoring, though the most compelling combinations usually come with an element of surprise, like sculptural jewellery or metallic hardware.
Fitted waist jacket, $359.90, Mango
A nipped-in shape keeps the tailoring sharp while leaving room for the skirt’s pleats to open beneath it.
Belted pleated woven grain de poudre maxi skirt, about $872, Self-Portrait at Net-a-Porter
Floor-skimming pleats make this feel closer to evening tailoring than everyday uniform.
The Vienna Collection necklace, $1,500, Swarovski
Oversized crystals bring enough bling to interrupt the good manners of grey tailoring.
3. With a Graphic Tee
Few wardrobe pairings work harder than a pleated skirt and a graphic tee, which is a combination that’s especially useful on mornings when your energy to dress up is in short supply.
Washed effect slogan t-shirt, $29.90, Zara
Graphic tees work best when they have a little history to them, even if it’s manufactured.
Chiffon pleated midi skirt, $49.90, Uniqlo
The sort of skirt that wears well with either a slogan tee or a buttoned-up Oxford shirt.
Haylen braided-charm tote bag, $99.90, Charles & Keith
Balance out the casual vibes with a structured shoulder bag in timeless yet fashion-forward espresso brown.
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4. With An Oversized Shirt and Sandals
A roomy button-down and sandals bring a certain ease to the structured silhouette of a pleated skirt, creating an ease that looks particularly modern.
Thick sole sandals, $55.78, Agsdon at LazMall
Think of platform sandals as the antidote to anything that feels overly ladylike.
Relaxed Forever t-shirt, $275, ME + EM
An oversized, relaxed fit is another secret to making a pleated skirt look modern.
Rohe pleated wool mid skirt, $1,010, Róhe at Farfetch
Sharp pleats and a wrap-style waist give this skirt a more architectural feel.
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5. With a Statement Belt
Play up the polish of a pleated skirt with a fine-knit top, and let a statement belt put a sharper crease in the look while cinching your waistline in the process.
Faux suede wide studded belt, $47.99, Pieces at ASOS
A wide belt gives a pleated skirt a more offbeat look, especially when punctuated with rows of metal studs.
Pleated midi skirt, $79.90, H&M
Soft pink keeps the silhouette feminine, though the sharp folds stop it from looking saccharine.
Brushed Merino wool polo jumper, $190, COS
Part polo shirt, part knitwear, and much more interesting than either sounds.
6. With a Cardigan and Heeled Boots
There is something satisfying about the contrast between a fuzzy cardigan and crisp pleats, especially when grounded with boots that give the look a little weight.
Pleated Skirt, $13.61, Zanzea at Shopee Mall
Gold-tone buttons lend this pleated skirt a slightly naval look, which only adds to its charm.
Ankle boots, $119.90, Pedro
Consider them the grounding force in an outfit full of texture and movement.
Cashmere cropped cardigan, $315, Everlane
The cropped length lands neatly at the waist, making it an easy partner for high-waisted pleated skirts.
7. With Denim and Romantic Ruffles
Pleated skirts need not only lean polished; paired with ruffles and denim, they take on a slightly offbeat charm that looks more personal than prim.
Annaelle ruffled silk-georgette top, $267, Isabel Marant at The OutNet
Ruffles this dramatic deserve something equally dramatic beneath them, such as a pleated skirt.
Esme safari style drawstring jacket, $346, Fabrique
You can always count on a washed denim jacket to keep ruffles and pleats from drifting too far into fairytale territory.
Thicker Bottoms 1 skirt, $234, Issey Miyake at Club21
A reminder that pleats can be playful, especially when rendered in a shade this vivid.
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