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

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Rosamosario Tulle Bustier Top

EB Denim Vintage Long Skirt

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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

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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

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Soldout.NYC The Not So Basic Tank in White

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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.

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? ›

You're most likely not going to be hitting up a restaurant where formal wear or dressy attire will be required. That is unless you are just the fancy type! 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.

How do you dress classy in your 20s? ›

Classic pieces are going to be your best friend. Start adding button down shirts, shirt dresses, blazers, chic flats or loafers or classic white sneakers to your closet. It's time to phase out of distressed pieces and short hemlines. Just above the knee hemlines should be the shortest you go.

How can I dress stylish in my 20s? ›

This is the time to invest in important go-to pieces that will form the foundation of your wardrobe years to come. Plus, it'll make you feel great every time you slip them on: hard-wearing trousers, good denim, solid shoes, your first proper suit and a decent watch. But this is also the time to experiment with trends.

What colour is best to wear on a date? ›

It's generally agreed that the safest colour to wear on a first date is black. It's universally flattering, inoffensive, and goes with anything, but it can also give little away about yourself which can be important on a first date.

How can I look more attractive on a date? ›

Both men and women are attracted to physical indications of health, such as shiny hair, clear skin, bright eyes, and a fit body. Try to have a symmetrical face. This can be hard to achieve at short notice, so it's a good idea to have your face sorted before you're asked out on a date. Having blue eyes also helps.

What is the best color to wear on a first date? ›

In other words, red and black were the preferred colors when dressing up for a date across the board, regardless of sexuality and gender. So, the next time you are dressing up for a big first date, take a look at your colors. Odds are you will be wearing a bit more red and black than usual.

What not to wear on date night? ›

Avoid wearing super low-cut tops and dresses that make you appear less like wife material and more like a one time fling. Instead of drawing attention to your chest, focus on your neck and shoulder area instead. The neck is one of the most vital areas of the body, both when it comes to survival and romantic attraction.

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.

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.

How to look rich but casual? ›

Always wear clean clothes, freshly pressed, with no threads, rips, stains, or fading. Black, white, navy are always elegant colours that can make you look more expensive. Match your outfit with some assorted accessories such as a couple of bracelets and a pair of sunglasses for that extra visual effect.

How to dress casually as a woman? ›

Whether you're going out with your friends or you're heading to the office on a casual Friday, a laid-back style is the best way to go. The casual dress code typically consists of jeans, T-shirts, and cardigans. If you prefer skirts and sneakers, go for them!

What is 20s fashion? ›

What were the fashion trends of the 1920s? The fashion trends of the 1920s were more casual and relaxed. Women often wore knee length tubular day dresses and men often wore knickerbockers with sweater vests. The flapper style for women and the zoot suits for men were also popular in the 1920s.

Can 20 year olds wear crop tops? ›

While crop tops are more widely accepted among teenagers and young adults, individuals of any age can choose to wear them based on their personal preferences.

What to wear in negative 20? ›

Following conventional wisdom, dressing in layers is the best approach, not only for staying warm outside but for easily adjusting to moving between indoors and out. Your outerwear, whether it's a coat or jacket, should be insulated to protect from the wind and rain.

How to look older at 20? ›

Wear neutral tones

Bright colors are really for younger people. The more colors you wear, the younger you'll appear. In order to look older, stick to neutral tones. Wearing black, grey, tan, brown, and the likes frequently will make you seem a lot older than you are.

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