The Tamesis
Photo: Phil Oh
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Some style staples are meant to be worn together, such as the classic white T-shirt and jeans, or the casual combination of a khaki windbreaker and penny loafers. We tend to see these dynamic duos on the street style circuit, and last March’s SS26 Paris show proved that certain combinations not only work, but win. (Hopefully FW26 will offer more of the same.) Enter: sneakers paired with a skirt. It’s a casual-cool dressing formula that feels tailor-made for the months we’re about to spend. You know those February days: chilly at breakfast, sunny at lunch, requiring a light jacket and a pair of shoes that aren’t sturdy lug soles. Paired with sporty sneakers, high-low contrasting polished midi trousers feel straight out of Miuccia Prada’s playbook, and are equally suitable for the 9-to-5, weekend errands, or even front-row moments.
“Vogue” Must-Buy Sneaker Styles
The best part? You probably already have the basics of this all-star duo. But if you’re ready to add something new, keep scrolling: below, discover the easiest, coolest ways to pair sneakers with a dress in no time.
Inherited cool
Pair a classic all-black Converse with a wrap-front pencil skirt from Victoria Beckham, a sleek leather blazer from Almina Concept, and a burgundy and white button-down top from The Frankie Shop for an instantly cool street-style ensemble. Finally, pair it with comfortable cashmere socks and Kallmeyer’s corded bag to create a model’s relaxed temperament when off work. A modern twist on traditional clothing, perfect for a Parisian sidewalk or a weekend in the city.
Sport mode
Show off your sporty side by pairing Wales Bonner’s hottest new sneakers with Alaïa’s drawstring shell skirt. On the upper body, put Uniqlo’s khaki short windbreaker over Sanderlak’s striped polo shirt to create a fresh, sporty look. Then, bring it back to fashion-girl territory with a suede tote from Nili Lotan and a burgundy leather bandana from Nour Hammour.
street style feel
From last season’s caramel colorway to this year’s neon yellow, Dries Van Noten’s It sneakers are a shoe that continues to evolve (and get better) with time. Right now, we recommend pairing it with a cherry red midi coat from Loulou de Saison, a leopard print coat from Toteme, and a simple white T-shirt from Cos. Finish with ribbed cashmere socks from Éterne and tassel earrings from Sophie Buhai for the ultimate chic-girl look.
modern preparatory
Prep’s influence continues to dominate. Create your own style with Jil Sander’s checked poplin midi shoes and Nike’s burgundy Daybreak sneakers, creating the perfect mix of polished and sporty styles. Then opt for elevated classics: a sophisticated zip-up sweater from Joseph, a buttery yellow tote from Bottega Veneta, and statement accessories from Lisa Yang and Thistles.
Sweet and fashionable
Sneakers and lace-trimmed slip dresses were two of last season’s biggest trends, and this vibrant combination is still going strong in 2026. Wear them with Tibi’s edgy biker jacket, J.Crew’s cashmere V-neck and Saint Laurent’s leopard-print calf hair tote. The result? It turns out that some fashion items are destined to stay at the top of your shopping cart.
Minimalism and Distortion
Everyone who calls themselves a minimalist seems to consider Asics sneakers their fashion secret weapon. Take inspiration from the Olsen twins and add an extra layer of effortless cool with a front-front jacket from Róhe, a gorgeous silk maxi skirt from Another Tomorrow and a rope necklace from Heaven Mayhem. Complete the simple look with cozy cable-knit socks from Petit Plume and a croc-embossed tote from Toteme.
pop of red
Make Puma’s hottest Speedcat sneakers your ultimate styling tip this season (and beyond). Pair it with a khaki pleated skirt from Róhe and a plaid button-down top from Zara for an elegant look, then throw on a shearling jacket from Arma for cozy coverage when the winter chill still sets in. Finally, pair it with DeMellier’s versatile leather handbag and a pair of Comme Si socks to give the entire uniform a fresh and fashionable feel.
Xiaohei everything
Like the little black dress, Adidas’ all-black Japan low-top sneakers and Cos’ A-line midi skirt also have endless styling potential. Wear it with a cozy shearling coat from Maria McManus, a second-layer turtleneck from Uniqlo, and a neatly knotted Le Scarf scarf at the neck for a ladylike look. Finish it off with Khaite’s multi-colored handbag for an unexpectedly simple pop of style.
