Milan Fashion Week Street Style Was a Masterclass in Skirt Styling

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Photographed by Phil Oh

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Out of all the back-to-back fashion weeks occurring during fashion month, Milan is always one of the most sophisticated and wearable street style scenes. Showgoers often look to transitional wardrobe heroes, like blazers, barn jackets, and walkable wedges to parade around town. However, this time, it was obvious that a Miuccia Prada effect was dominating the street-style scene yet again. Skirts, skirts, and more skirts were in abundance—from semi-sheer styles to pleated silhouettes, a mainstay for Prada herself, of course.

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With 153 events on the schedule, the street style set opted for those stylish everyday pieces that are less trendy while remaining fashion-forward. You know the pairings—the cool-girl barn jacket teamed with a lace midiskirt, a sporty bomber complemented by a checked skirt, and loafers, and a sheer slip skirt amplified by fresh colorways found on the spring/summer 2025 runways. For tips on how to wear your skirts this season, take note from Ms. Prada and the Milan Fashion Week crowd, ahead. Ciao!

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Photographed by Phil Oh

Pair a Barn Jacket with a Lace Slip

Lace is inherently fancy—it often trims the borders of party-ready items and evening styles. But, it doesn’t have to be. Tone down the feminine details by wearing a casual waxed cotton jacket and a white T-shirt—less is more.

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Alex Mill

Chiltern Street waxed cotton jacket

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Leset

Margo cotton-jersey T-shirt

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LoveShackFancy

Malina lace-trim midi skirt

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Saint Laurent

Feminine Fashion Icons SL 567 oval sunglasses

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Prada

belted buckle bag

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Photographed by Phil Oh

Give a Checked Skirt a Sporty Update

Windbreakers, soft shells, anoraks, and zip-up jackets were spotted on nearly every runway, and the tones are leaning further and further into athleisure. Contrast your checked skirt with a cropped parka jacket, then add the playful accessories. Think, buckled loafers, an oversized scrunchie, and a patent leather bag from Khaite.

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Jacquemus

The Caraco cropped parka

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Bottega Veneta

wrap-effect checked cotton-blend tweed midi skirt

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Marni

Bambi 3.0 loafers

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Uniqlo

HEATTECH knitted tights

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Khaite

Lori baguette bag

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Emi Jay

silk scrunchie

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Photographed by Phil Oh

Go Classic with a Leather Midiskirt

The leather midiskirt’s versatility knows no bounds—there are so many ways to style one. One of the ways we’ll be sporting the look this season is with classic wardrobe essentials in fresh new shapes. Trade in your wrap coat for a cocoon silhouette, and set aside your knee-high boots for a modern wedge heel.

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The Row

Verlain silk-wool open jacket

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Everlane

The Box-Cut tee

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Co

Leather belted front split midi skirt

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Toteme

black zip leggings

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Toteme

suede wedges

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Cos

Cavatelli clutch

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Photographed by Phil Oh

Play with Springs Favorite Color Combinations

Spring is on the way, and with it comes refreshing color combinations to pull you right out of winter’s endless slump. Pale pink and pale yellow are an airy blend of pastels that feels warm-weather ready. Keep warm with a blue knit underneath.

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Zara

cotton jacket

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The Frankie Shop

Heidi semi-sheer midi skirt

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J.Crew

cashmere classic-fit crewneck sweater

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The Row

90s baguette bag

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Blue Nile

diamond stud earrings

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Loewe

Petal bow metallic leather sandals

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Photographed by Phil Oh

Embrace a Prep Moment

School is in session! And the fashion set still feels nostalgic for collegiate codes by way of tracksuits, plaid prints, and loafers. The star of the show? The boat shoe! Thanks to the scholarly staples found at Miu Miu and Prada, we’re wearing ours with pleated skirts, barn jackets, and more.

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J.Crew

canvas barn jacket

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Proenza Schouler

Felicity strapless layered ruched crepe top

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Miu Miu

Sienna unlined leather boat shoes

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Massimo Dutti

asymmetric pleat midi skirt

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Banana Republic

wide leather waist belt

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Porto Studio

The Pouch

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Photographed by Phil Oh

Add Some Everyday Embellishments

Stop saving your sequins, crochet, and metallic high-shine for special occasions—it is time to hone in on the art of wearable preciousness. Tone down the moment a notch with pared-back sporty basics, like a striped polo sweater and a simple navy blue blazer.

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Aritzia

Lomu polo longsleeve

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Prada

satin mules

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Bottega Veneta

aviator-style acetate sunglasses

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Zankov

Matteo skirt

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Mango

fitted suit jacket

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Agmes

Cora recycled silver and cord necklace