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Some style staples are simply meant to be worn together—like the classic white tee-and-jeans formula, or the off-duty-approved pairing of a khaki trench and penny loafers. We tend to spot these dynamic duos in heavy rotation on the street style circuit, and last March’s SS26 Paris shows proved that certain combinations don’t just work—they win. (Here’s hoping FW26 delivers more of the same.) Enter: sneakers with skirts. It’s the casually cool outfit equation that feels tailor-made for the in-between months we’re about to navigate. You know the kind of February day in question: freezing at breakfast, sunny by lunch, calling for light outerwear and a shoe that isn’t another sturdy lug-sole. The high-low contrast of a polished midi styled with a sporty trainer feels straight out of the Miuccia Prada playbook, equally suited for your nine-to-five, weekend errand runs, or even a front-row moment.
Vogue’s Must-Shop Sneaker Styles
The best part? You likely already own the building blocks of this all-star duo. But, if you’re ready to add something new, keep scrolling: below, discover the easiest, coolest ways to wear sneakers with skirts right now.
Heritage Cool
Style classic all-black Converse with Victoria Beckham’s wrap-front pencil skirt, Almina Concept’s sleek leather blazer, and The Frankie Shop’s burgundy-and-white button-up for an instantly cool, street style-ready mix. Finish with cozy cashmere socks and Kallmeyer’s corded bag for that model-off-duty ease. Perfect for Parisian pavements or a weekend in the city, it’s heritage dressing made modern.
Sport Mode
Lean into your sporty side by pairing Wales Bonner’s hottest new trainers with Alaïa’s drawstring shell skirt. Up top, layer Uniqlo’s khaki cropped trench coat over Sanderlak’s striped polo for a fresh, athletic-leaning finish. Then, bring it back to fashion-girl territory with Nili Lotan’s suede tote and Nour Hammour’s burgundy leather bandana scarf.
Street Style Sensations
From last season’s caramel colorway to this year’s neon yellow, Dries Van Noten’s It sneakers are the kind of pair that evolves (for the better) with time. Right now, we’d recommend wearing yours with Loulou de Saison’s cherry-red midi, Toteme’s leopard-print coat, and Cos’s easy white tee. Finish with Éterne’s ribbed cashmere socks and Sophie Buhai’s tassel-adorned earrings for a final fashion-girl flourish.
Modern Prep
Prep’s influence continues to reign. Make it your own with Jil Sander’s checkered poplin midi and Nike’s burgundy Daybreak sneakers for a polished-meets-sporty finish. Then lean into the elevated classics: Joseph’s refined zip-up sweater, Bottega Veneta’s butter-yellow tote, and statement accessories from Lisa Yang and Thistles.
Sweet Sleek
Sneakerinas and lace-trimmed slip skirts were two of last season’s biggest trends—a dynamic duo that’s still going strong for 2026. Style them together with Tibi’s edgy moto jacket, J.Crew’s cashmere V-neck, and Saint Laurent’s leopard-print calf-hair tote. The result? Proof that some fashion favorites are simply meant to stay at the top of the carts.
Minimalist With a Twist
Every self-proclaimed minimalist seems to credit Asics sneakers as their style secret weapon. Take cues from the Olsen twins and wear yours with Róhe’s toggle-front jacket, Another Tomorrow’s sumptuous silk maxiskirt, and Heaven Mayhem’s corded necklace for that extra dose of effortless cool. Complete the pared-back look with Petit Plume’s cozy cable-knit socks and Toteme’s croc-embossed tote.
Pop of Red
Make Puma’s red-hot Speedcat sneakers your ultimate styling hack this season (and beyond). Pair them with Róhe’s pleated khaki skirt and Zara’s plaid button-up for a polished twist, then layer on Arma’s shearling jacket for cozy coverage when the winter chill still lingers. Finish with DeMellier’s wear-with-everything leather tote and a pair of Comme Si socks to keep the whole uniform feeling fresh and updated.
Little Black Everything
Like an LBD, Adidas’s all-black Japan low-top sneakers and Cos’s A-line midiskirt have endless styling potential. Wear them together with Maria McManus’s cozy shearling coat, Uniqlo’s second-skin turtleneck, and–for a ladylike nod–Le Scarf’s silk scarf knotted neatly at the neck. Finish with Khaite’s multicolor tote for a perfectly unexpected, maximalist pop.
