20 Fresh Date Night Outfit Ideas From Street Style

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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.

Tulle Bustier Top

Vintage Long Skirt

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.

Pointelle Clasp Cami

Pointelle Clasp Skirt

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.

Jennifer Crochet Cotton Mini Dress

Leonie Lambskin Bow Ballerina Flats

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.

Ida Tee AB x TO

Sequined Miniskirt

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.

Morgan Cropped Cotton Shirt

Isla Natural Linen Cargo Maxi Skirt

A Little Noughty

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.

Halterneck Wraparound Silk Dress

Carina 110 Canvas & Jute Espadrille Wedges

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.

The Not So Basic Tank in White

The Romy Pant

All-In Asymmetric

Asymmetrical necklines are dominating the most imaginative pieces of the season, and the options transcend categories. Tank tops, miniskirts, denim, and everyday dresses are being modernized with this deconstructed detail, an easy way to capture attention on an evening out.

Remmy Barbie Pink Mini Dress

Balla Mesh Flats

A Monochromatic Statement

These days, all-black outfits are anything but boring. Our favorite contemporary brands have revisited the non-hue hue time and time again, giving it new life with asymmetric details, cold shoulders, and oversize silhouettes. Pair a statement top with black trousers for an evening look that could also work in the daytime.

One-Shoulder Draped Satin Top

Ssense Exclusive Black Trousers

Pencil Me In

The practical pencil skirt can be worn season after season, but it’ll never exhaust you. With current but timeless details, like an all-over logo, oversize pockets, and sheer fabrics, these skirts will become wardrobe staples beyond the office. Make yours an everyday option with a cropped tank.

Sheer A-Line Midi Skirt

Patent Leather Trimmed Skirt

Match Made in Heaven

There’s nothing quite as effortless as a matching set. Just as comfortable as a maxi dress, and just as sophisticated as a pair of pleated trousers, the right matching set comes in a variety of designs—from winter-white options to vacation-ready summer sets.

Blaire Halterneck Top

Coordinating Skirt

On the Fringe

Embellishing garments with fringe first became popular in the 1920s as part of the flapper era—and then it got a major makeover. These days, fringe can be just as modern as it can be edgy, with offerings from By Malene Birger to Saint Laurent. Go for neutral cool with a fringe-embellished dress, and keep it contemporary with a pair of Margiela flats.

Fringed Dress

Tabi Flat

Pattern Play

Mixing prints is here to stay, if you’re bold enough to attempt it. The key to acing this trend? Combine prints in the same tonal range. A more polished look can be achieved by taking this route—think burnt orange with pale orange and sherbet hues.

Oblique Short Sleeve Shirt

Monogram Pareo

A Little Naughty

A never-ending ’90s craze has us continually revisiting iconic slipdress moments from the past, from Naomi Campbell to Kate Moss. Mostly everyone has a slipdress they turn to in their closets, making it the ideal piece to refresh for a date. Take the street-style route and team yours with vintage-inspired heels, preferably a metallic pair.

Tulip Satin Maxi Dress

Mini Annie in Metallic Gold

Summer Staples

For dates that occur outside this season, look no further than the pieces already in your warm-weather rotation. A classic tank top and cotton white midi skirt will suffice for ice cream, beach lounging, and walks through the park.

Ribbed White Tank Top

A-Lined Midi Skirt

Ruched Romance

One trend worth citing is the surplus of ruffles worn by women and men lately. From silk textured blouses to cinched maxi dresses, ruffles and ruching have managed to become both feminine and edgy. Pair them with a billowy bubble hemline for a fashion-forward date night outfit.

Tess Ivory Bodysuit

Cropped Wide-Leg Trousers

In-Vested in You

Over the past few seasons, the suit vest has shifted from a workwear staple to a summer wardrobe essential, and the options are endless. They work well with trousers, maxi skirts, denim, and even a pleated mini for a modern schoolgirl look.

Gelso Woven Waistcoat

High-Waisted Asymmetric-Hem Skirt

A Sheer Chance

There is power in transparent clothing: Nensi Dojaka, Prada, Ferragamo, and even Rodarte have experimented with nuanced nudity in recent collections. For those bold enough to test it out (bravo, ladies!) despite the sensationalism, opt for a sheer dress with complementary, full-coverage undergarments.

Keyhole Cotton-Blend Chiffon Dress

Derin Sheer Draped Dress

Work and Play

Although social media will occasionally try to convince us that wearing a blazer “everywhere” is passé, we have to disagree. A blazer works for every occasion, including date night dressing. Wear your favorite oversize silhouette atop a silky slipdress, then add sneakers for a playful tone.

Corrin Ivory Blazer

Crepe Maxi Dress

The Go-To Combo

Failproof, effortless, and comfortable—the classic denim-and-tank-top pairing will never be the wrong option, no matter the occasion. To dress it up a bit, choose a tank top with some texture for added interest, and jeans that hang loose around the hip.

Square Sleeveless Tank Top

The Danielle Stretch Jean

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