20 Fresh Date Night Outfit Ideas From Street Style (2024)

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

20 Fresh Date Night Outfit Ideas From Street Style (1)

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

20 Fresh Date Night Outfit Ideas From Street Style (2)

Rosamosario Tulle Bustier Top

EB Denim Vintage Long Skirt

20 Fresh Date Night Outfit Ideas From Street Style (3)

EB Denim Vintage Long Skirt

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A Textured Two-Piece

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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 Skirt

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Christopher Esber Pointelle Clasp Skirt

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An Upper East Side Take

20 Fresh Date Night Outfit Ideas From Street Style (7)

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

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Anna Kosturova Jennifer Crochet Cotton Mini Dress

Loeffler Randall Leonie Lambskin Bow Ballerina Flats

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Loeffler Randall Leonie Lambskin Bow Ballerina Flats

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A Mini Moment

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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

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Anine Bing Ida Tee AB x TO

Guizio Sequined Miniskirt

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Guizio Sequined Miniskirt

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The New Cargo

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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

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Rag & Bone Morgan Cropped Cotton Shirt

Dissh Isla Natural Linen Cargo Maxi Skirt

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Dissh Isla Natural Linen Cargo Maxi Skirt

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A Little Naughty

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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

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Raey Halterneck Wraparound Silk Dress

Castañer Carina 110 Canvas & Jute Espadrille Wedges

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Castañer Carina 110 Canvas & Jute Espadrille Wedges

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Head-to-Toe Essentials

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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

20 Fresh Date Night Outfit Ideas From Street Style (20)

Soldout.NYC The Not So Basic Tank in White

20 Fresh Date Night Outfit Ideas From Street Style (2024)

FAQs

What is the perfect date outfit? ›

You want your outfit to feel as laid-back as the date. "Opt for a casual, easy vibe," Priyanka says. "Keeping it low-key is the main focus." As jeans are practically the definition of casual, they're an ideal choice. "Light-wash, high-waist denim with a T-shirt is a great look and also very classic," Priyanka notes.

What is date night dress code? ›

Cute and casual date night outfits can be as basic as jeans and a graphic t-shirt to dresses and flirty sandals for the ladies. For men, jeans are most common and are easy to elevate with a crisp button-down shirt or a sport coat over a tee.

How do I choose a date outfit? ›

According to Experts, Here's What to Wear on a First Date to Get a Second One:
  1. Wear Something That Makes You Feel Confident.
  2. When in Doubt, Wear Red or Black.
  3. Avoid Wearing Orange and Brown.
  4. Wear Something Comfortable and Practical.
  5. Show Off Your Neck Instead of Your Chest.
  6. Avoid Looking Overly Trendy or Unapproachable.

What do you wear for a date night at home? ›

A classic button-up and jeans

This outfit combination is sure to make you feel put-together while requiring the least amount of effort. Paired with a ribbed tank or baby tee, you'll be ready for date night at home in a matter of minutes.

What Colour is best to wear on a date? ›

Black is your go-to colour. A new study by Britain's University of Lincoln suggests that black beats red as the colour of choice when it comes to finding new love. The study explains how red increases the perceived sexual receptivity of the wearer, while black increases how fashionable the person is thought to be.

How to dress well as a lady? ›

One of the most important parts of dressing like a lady is showing skin sparingly. You don't have to only wear pants and shirts with high necklines, but try not to expose too much cleavage or wear skirts and shorts that are super short. It's also a good idea to avoid wearing excessively tight clothing to stay classy.

What should date night look like? ›

A date night is an occasion where a couple dedicates time to be spent together, usually alone, with the purpose of reconnecting and bonding. A date night usually consists of a main activity, such as a dinner and/or a movie, or a few activities planned one after the other.

What outfits do guys like on dates? ›

What Clothes Do Guys Like on a Girl? 13 Outfits He'll Love
  • Backless dress or top.
  • Perfect pair of jeans.
  • Little black dress.
  • Cozy sweater dress.
  • Mini skirt.
  • Anything lacy.
  • White sundress.
  • Leather jacket.

How do girls dress for a date? ›

A midi-length dress and strappy heels are perfect for a dinner date. A strappy floral dress will go well with sandals if you are headed to a park. A casual sport fit is perfect for a sporty activity like bowling. A crop top and a pair of jean pants are perfect for a club date paired with sneakers and a sling bag.

What should a 50 year old woman wear on a date? ›

A silk blouse or a V-neck sweater with low heels or pointy flats looks feminine and polished; a simple white T-shirt or crisp white shirt with sleeves turned up and rolled with leather ankle boots looks classy and classic. White jeans with a black blouse or sweater and your black belt are always memorable.

What do you wear to a simple night out? ›

Try a slip dress paired with sliders or trainers, or a blazer paired with your favourite pair of jeans. You can also go all out and find your favourite bodycon dress, slick your hair back into a bun and add some chunky jewellery and accessories - adding a playful element to your look.

What not to wear on first date? ›

While some of us tend to look overly sexy on a first date, others tend to be way underdressed. Even if you have a bikini-ready body, do not wear leggings, a hoodie, or your worn-out sneakers on your first date. You'll give the impression that you have no interest in putting forth the effort to look nice.

What should I dress like for the first date? ›

Eye-catching pieces make a great impression, too, be it a uniquely cut top, printed pants, or sculptural earrings. Depending on the date, you can opt for elevated casual looks, like white sneakers with a dress, or a T-shirt and jeans with a pair of pastel kitten heels.

What guys should wear on first date? ›

It's All About the Fit

The last thing you want is your date to be distracted by your loose and baggy getup. Typically, a fitted (but not skin-tight) silhouette—where your clothes hug but not constrict your body—is the way to go. Look for items like a tailored dinner jacket, straight-leg jeans or slim button-down shirt.

What is the most iconic first date ideas? ›

First Date Ideas
  • Just do dinner!
  • Cook together.
  • Go for a stroll.
  • Walk shelter dogs.
  • Get breakfast.
  • Make a sweet deal.
  • Bust out the board games.
  • Hit up an arcade.
Feb 8, 2024

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