How to Street Style Your Summer Dress Like You Mean It

Summer dresses. The phrase conjures up sleepy meadows and girls with hair like satellite dishes for sunlight. But this is the city, darling—not a Taylor Swift music video. Here, your sundress needs teeth. It needs context. It needs a reason to be loitering outside a corner store at 11am with a bottle of San Pellegrino and an attitude problem.

Let’s start with the obvious: the Bottega Veneta slip dress. Whisper-thin and humming with quiet wealth, it's practically lingerie with a diploma. Now imagine it grounded with a pair of beat-up Sambas and a nylon Prada belt bag slung across your chest like a rejection letter from corporate life. Add wraparound shades if you're feeling apocalyptic.

Street style is, after all, about contradiction. Take the floral dress—once a symbol of girlhood and allergy season—and weaponize it. Look to Marine Serre, where dystopia flirts with hyperfemininity. Throw one of her moon-printed second-skin tops under a baby-pink broderie dress and top it off with a biker jacket that says, “I steal chargers.”

Then there’s the maxi moment. The Row does long and languid like it’s a legal requirement. Their cotton dresses, draped just so, beg for drama. Think: platform flip flops that look like they were made from car tires, a monastic bun, and an aggressive tote bag large enough to hold your ennui.

Key tip? Don’t chase polish. Imperfection is the point. Let your bra strap show. Mix high and low like you’re trying to confuse your tax bracket. A $1,200 dress with corner shop flip flops? Iconic. Lip gloss that’s mostly just Vaseline and ambition? Necessary.

And remember: summer isn’t just a season, it’s an aesthetic loophole. A time when exposing 70% of your body in a see-through mesh number while holding an iced oat latte is considered not just acceptable, but aspirational.

So wear the dress. But wear it like you’re late to band practice in 2003 Berlin. Or like you're on your way to dump someone at a rooftop party. Either way, wear it like you mean it—and don’t forget the sunscreen.

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SHOP THE STYLES

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Images

• Christian Vierig/Getty Images

• Pierguido Grassano

• Su Shan Leong/WWD

• Julia Spicer

• Launchmetrics Spotlight