Romance was once associated with girlishness and whimsy alone, and that bled into the way we presented ourselves on dates. In 2023, we’re no longer rejecting personal style for romantic encounters—in fact, we’re wearing outfits that reflect our ripened perspectives. The best date night outfits aren’t exclusive to an LBD. Personalized looks that embody individual auras are leading the way, for both men and women. Sheer dresses now hold as much power as a flouncy Cecilie Bahnsen midi, and suit sets are just as alluring as a plunging neckline—depending on who’s looking, and who’s wearing it. The best part about fashion is that it is an art, and art is subjective. Fashion is feeling, and feeling is sexy. Isn’t that romantic?
Caitlin Burke, a stylist and creative consultant, uses date night outfits as an opportunity to have more fun with styling. She opts for pieces that work as conversation starters. “I gravitate toward brands and pieces that can look simple at first, but something about them makes you look a bit longer or invites a question about what you’re wearing,” Burke tells Bazaar. “Whether it be an interesting cut, proportion, embellishment, or detail—fashion can be a form of flirting.” Some of her favorite brands for achieving that? “Christopher Esber, Khaite, Victoria Beckham, Proenza Schouler, and Jil Sander—especially for jewelry and accessories.”
For a late-night wine bar meet-up, opt for a knitted two-piece set and neutral-heeled sandals. Grabbing a nibble before movie night? Pair your favored T-shirt with an eye-catching mini. There is no incorrect way to do date night dressing, but if you’re stuck on date night outfit ideas, look to the 20 best outfits below from the stars of street style for inspiration.
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.
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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
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Christopher Esber Pointelle Clasp Skirt
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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.
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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
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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.
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
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.
