Here's How Cool Girls Are Wearing Dresses With Sneakers This Summer

Is there any summer outfit combination as cool, comfy, and effortless as a dress paired with sneakers? Whether it's a floral minidress with a crisp white pair of Converse or a silk slip dress with chunky kicks, it's the perfect duo that exudes a cool, carefree, "ready for anything" vibe. It allows for playfulness and self-expression in your ensemble because there are endless styles, colors, and combinations. Not to mention, it’s one of the easiest and comfiest outfit formulas to have on rotation.
If you're looking to give your dresses and sneakers a fresh and modern update this season, take a look at some of the coolest dress-and-sneaker outfits we've spotted on the fashion crowd this warm-weather season, and get the look with our shopping picks. We guarantee this will be your go-to combo for the sunny season ahead.
Add a comfy-cool vibe to a pretty floral minidress this summer. Finish the look with a sporty baseball hat.
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We love the idea of contrasting a romantic milkmaid dress with a pair of retro-cool sneaks.
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Give your floral midi dress a sporty edge with hiker-style sneaks—the perfect combo of practical and chic.
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Sporty sneakers add a playful touch to a sleek midi dress. Don't forget to add chic gold jewelry for the perfect finishing touch.
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For a picnic-perfect outfit, opt for white sneakers and a gingham dress.
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All a basic stretchy tank dress needs is a pair of cool Converse.
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Give a pretty floral maxi dress a casual spin with plain white kicks. Add a trench coat when it's cooler out.
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Vintage Nikes pair surprisingly well with a breezy white summer dress.
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Contrast colors and opt for a sunny yellow dress paired with a vibrant blue pair of kicks.
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A striking red slip dress looks all the cooler with a pair of Converse high tops—perfect for a bike ride in the city.
Up next, 24 Dreamy Dresses for Your Most Romantic Summer Yet

Judith Jones is the associate shopping director at Who What Wear and has worked in fashion for over a decade. She specializes in shopping content and trend stories with high-affiliate impact. She shares the coolest, most desirable fashion market finds and brands for every budget. Previous to working in fashion, Judith worked as a TV host on the PBS travel show Globe Trekker (airing on Netflix and Amazon Prime) sharing her passion for travel and culture.
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