20 Best Date Night Outfits for Summer 2024

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Show Some Leg

The best thing about a denim skirt is its timelessness. Despite getting makeovers in the form of new lengths, high-slit details, and embellishments, the denim maxi skirt remains a transitional piece you can wear every season. For date night, team yours with a bustier.

Rosamosario Tulle Bustier Top

Rosamosario Tulle Bustier Top

EB Denim Vintage Long Skirt

EB Denim Vintage Long Skirt

Now 40% Off

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A Textured Two-Piece

Nothing conveys ease like a matching set, and our favorite options come with ample details—like a pleated skirt and button-embellished long-sleeved top from Christopher Esber.

Christopher Esber Pointelle Clasp Cami

Christopher Esber Pointelle Clasp Cami

Now 50% Off

Christopher Esber Pointelle Clasp Skirt

Christopher Esber Pointelle Clasp Skirt

Now 50% Off

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An Upper East Side Take

Although date night dressing goes well beyond the little black dress, it’s still a chic option to keep in rotation. Choose one with modern details, like a sheer skirt, cutout shoulder, or a mini length.

Anna Kosturova Jennifer Crochet Cotton Mini Dress

Anna Kosturova Jennifer Crochet Cotton Mini Dress

Loeffler Randall Leonie Lambskin Bow Ballerina Flats

Loeffler Randall Leonie Lambskin Bow Ballerina Flats

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A Mini Moment

Thanks to brands like Miaou and Miu Miu, the micro miniskirt resurgence isn’t showing signs of slowing down, despite how polarizing it tends to be. To balance a statement sequined mini, pair it with a casual graphic T-shirt.

Anine Bing Ida Tee AB x TO

Anine Bing Ida Tee AB x TO

Guizio Sequined Miniskirt

Guizio Sequined Miniskirt

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The New Cargo

Maxi, midi, mini, and denim—the cargo skirt has returned in eclectic silhouettes that modernize this early-’00s trend. One thing that makes it more attractive, in addition to the nostalgic vibe, is how easy it is to style. Tank tops, button-ups, sneakers, and mules all pair well with this must-have.

Rag & Bone Morgan Cropped Cotton Shirt

Rag & Bone Morgan Cropped Cotton Shirt

Dissh Isla Natural Linen Cargo Maxi Skirt

Dissh Isla Natural Linen Cargo Maxi Skirt

Now 76% Off

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A Little Naughty

Besides the classic slipdress, there’s nothing more symbolic of the 1990s than the black halter-neck dress. Team yours with another ’90s staple, the slip-on wedge, for a comfortable yet sensual date night look.

Raey Halterneck Wraparound Silk Dress

Raey Halterneck Wraparound Silk Dress

Castañer Carina 110 Canvas & Jute Espadrille Wedges

Castañer Carina 110 Canvas & Jute Espadrille Wedges

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Head-to-Toe Essentials

In the midst of summer, when outfit ideas are running thin and temperatures are skyrocketing, we always have the essentials to fall back on. A classic tank top—now as much of a luxury item as it is a basic—paired with well-fitting trousers is a match that knows no bounds. Stay logo-less, or indulge in Loewe or Miu Miu’s insignia-stamped options.

Soldout.NYC The Not So Basic Tank in White

Soldout.NYC The Not So Basic Tank in White

Cortne Bonilla is freelance writer who occasionally dabbles in party reporting. When she’s not writing, you can find her vintage shopping, sipping iced lattes, reading on the train, and indulging in Pilates. 

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