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Behold: 20 Easy Date Night Outfit Ideas to Keep in Your Back Pocket

From casual to candlelit vibes

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Date Night Outfit Ideas: collage of various street style images of women in fashionable outfits
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Putting together a date night outfit can be stress-inducing and cost you precious time that you can’t afford to sacrifice. There’s nothing quite worse than when the panic sweat kicks in as you watch the clock tick down during your umpteenth outfit change. Fret not, daters! Whether you’re dressing for a first date, heading to a second date or in the throes of a lasting relationship, we’re here to help you create a swoon-worthy ensemble that elicits a double-take. From casual cocktails to a candlelit evening and everything in-between, here’s a list of 20 easy date night outfit ideas to reference and recreate for any and every vibe. Enjoy your sexy night out in style.

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date night outfit ideas Little Black Dress
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1. Always, Always, Always a Little Black Dress

When in doubt, you can’t go wrong with a LBD. Classic and timeless, this versatile and flattering option will carry you through a wide range of dates, from dinner and drinks to a cooking class to a Broadway show and beyond. Material matters, so consider the season and activity. A tousled linen will be wise for a summer picnic while a luxe velvet will look refined in the colder months. Finish with a slinky and sexy pair of kitten or slingback heels and, while you’re at it, don a playful baguette bag a la Carrie Bradshaw.

date night outfit ideas A Cozy Sweater
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2. Snuggle Up in A Cozy Sweater

A coffee date calls for comfortability, and nothing screams comfy quite like a cozy sweater. The key to nailing this look is to choose what best complements your body, so play around with proportions, color, print, embroidery, embellishments, cut, sleeve type and fit until you find one that suits your style. Combine it with a skirt, trousers or jeans, or layer it over your favorite dress to complete your casual and cute ‘fit.

date night outfit ideas Something Smocked
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3. Stick with Something Smocked

It’s all in the details, people, and if you want your date to read between the (smocked) lines, there’s a lot to be said when ruching is at the helm of the ‘fit—dirty talk aside. Often gathered and sometimes embroidered, a smocked bodice can be an ideal way to create a form-fitting silhouette that’s ultra-flattering and forgiving, hiding any insecurities.

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date night outfit ideas A White Blouse and Jeans
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4. A White Blouse and Jeans Combo Is Forever Timeless

Tried-and-true for a reason, a white blouse and jeans combo can seem so simple yet go so far, especially if it’s a spontaneous or unplanned date. Yes, a plain white T-shirt may be one of your staples, but challenge yourself to swap it for a white blouse instead. A fancier top can easily elevate your usual look while offering up the same familiarity you gravitate towards, plus the jeans keep it totally caszh. Don’t forget to play around with texture and accessories if you want to showcase more of your personal style; an exaggerated collar or split-hem jean will do the trick.

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The Shirt by Rochelle Behrens
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date night outfit ideas Sexy Blazer Dress
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5. Book a Meeting with That Sexy Blazer Dress, Stat

Traditional workwear can go beyond the four walls of an office cubicle when styled as a dress. Whether you opt for a tailored silhouette or choose the oversize route, the dramatic shoulders, structured lapels and traditional button closures in a blazer dress will make a bold and powerful impression on any date night. Take it one step further with your pick of opaque, sheer or fishnet tights to create the illusion of elongated legs.

date night outfit ideas a Leather Jacket
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6. Get Grungy in a Leather Jacket

Chilly weather in the forecast? Good news: You don’t have to sacrifice fashion for warmth. A leather jacket can keep you cozy enough while introducing an element of grunge and edginess—especially if it has an interior lining. What’s more, there are a myriad of styles to choose from—motorcycle, biker, vintage, bomber, etc.—so be sure to select one that complements both your outfit and taste.

date night outfit ideas a Matching Suit Set
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7. Show ‘Em Who’s Boss in a Matching Suit Set

Self-confidence is sexy, and what better way to exude that than in a matching suit set? When it comes to a power get-up, there’s a fine line between cool and corporate, so a pop-of-color, tailored silhouette or relaxed fit can be enough to maintain a flirty and playful vibe. (Psst…don’t forget the strappy heels, either.)

date night outfit ideas a Comfortable Knit Dress
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8. Embellish a Comfortable Knit Dress

Casual, comfortable and totally charming, a knit dress, whether it’s sleeveless or long-sleeved, mini or maxi, bodycon or relaxed, can be a saving grace in cool temperatures. If you want to zhuzh up your outfit, a statement belt can create more dimension and accentuate the smallest part of your waist, highlighting your natural figure. There’s plenty of flexibility in footwear department, too, so don’t be afraid to wear your most comfortable sneakers if you aim to tone it down for the date.

date night outfit ideas Leather Pants
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9. Get Leggy in Leather Pants

When a leather jacket isn’t enough leather for you, opt for leather pants instead. They’re a sleek and stylish swap of your usual denim bottoms, and they’re quite bold already, so we suggest styling them with a shoe of the same hue and a simple blouse up top. Psst…go ahead and enjoy that extra 30 minutes of bliss with a glass of vino before your date picks you up instead of tearing your closet apart to find a ‘fit.

date night outfit ideas a Cardigan and Jeans
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10. All Hail a Cardigan and Jeans Uniform

If we’ve learned anything from Taylor Swift recently, it’s that a simple sweater combo can look incredibly endearing and desirable. Whether you’re freshly dating or a few years into a relationship, a cardigan styled with jeans makes for an understated and relaxed date night outfit that’ll look put-together during mini golf, dinner, drinks or a coffee date. Choose a split hem or bold pattern for an interesting twist.

date night outfit ideas a Slinky Slip Dress
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11. Spice It Up in a Slinky Slip Dress

Who says slip dresses are strictly for the bedroom? (Not us.) In fact, a slinky slip dress is one of the sexiest ways to spice up your date night without—you know—showing up in literal lingerie. Bonus points if the dress has lace details or a corset bodice, but be careful as not to err too risqué. Hot tip: Adding a long wool coat or clean-cut blazer can help curtail overt suggestions and make for a sophisticated and classy look.

date night outfit ideas a Pop of Red
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12. Turn Up the Heat in a Pop of Red

Red is on fire (pun intended) right now, having its moment in the limelight as both the top color of the season and one of the most sought after winter fashion trends. It’s daring, bold and confident, so make it a point to go all-in if you dare and have fun with it, whether that be in the form of a bodycon dress, bold red lip a la Taylor Swift or candy-apple stiletto peaking under a dark denim jean.

date night outfit ideas a Jumpsuit
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13. Slip into a Jumpsuit If You’re Crunched for Time

To make matters simple, try slipping into a jumpsuit for the big date. From denim to sequins to utility, there are a number of variations to choose from, not to mention plenty of opportunity to dress it up or down with layering, accessories and shoes. If your jumpsuit has an arresting pattern, you might want to consider casual tailoring. Alternatively, a striking pair of heels or knee-high boots with a waist-defining belt would do wonders for a basic jumpsuit.

date night outfit ideas Oversize Shirtdress
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14. Make Like Bradshaw and Rock an Oversize Shirtdress

We’ll forever be taking style cues from Sex and the City, and one of Carrie Bradshaw’s most iconic looks of season three was when she transformed her ex’s Oxford button-down into a belted dress. Effortlessly sexy, a large, boxy and oversize shirt can feel fresh, modern and entirely flirtatious (especially if it was borrowed from your date).

date night outfit ideas a Fitted Tee
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15. Start Styling Around a Fitted Tee

After spending some time combing through racks of clothes for the perfect piece, sometimes it’s the simplest option that can take you for surprise. Case in point: the fitted tee. If you want to emit a relaxed, laid-back attitude for your date night at the comedy club, then this look is calling your name. We love that a fitted tee simultaneously shows off your figure while affording both comfortability and coverage—not to mention a bit of creative freedom for a daring pant pairing. Feeling adventurous? Show off your midriff in a crop. Want a conversation starter? Whip out that graphic T-shirt you grabbed at the flea market five years ago.

date night outfit ideas a Maxi Dress
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16. Go the Lengths in a Maxi Dress

In case you need to hear this: Maxi dresses aren’t strictly reserved for formal events. That’s right, a floor-length dress speaks volumes, letting your date know that you’ve gone the lengths (literally) to put in effort. Figure-hugging silhouettes, loud prints and revealing necklines are just a few options that would suit a cheeky night out.

date night outfit ideas Metallics
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17. Shine Bright in Metallics

Not for the faint of heart, this trend may be easier to wear than you might initially think. Start small with the addition of a metallic accessory or shoe, or dive into the deep end with a shimmering pant or slip dress. Try to balance it out with competing textures and dark fabrics, like a grounding wool or classic denim. (Hot tip: Avoid tacking on too much glitz, sequins, frills and noise elsewhere.) In a few years, when he thinks back, we guarantee that he'll recall what you wore on your first date.

date night outfit ideas Blue Satin Off-the-Shoulder Top
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18. There’s No Cold Shoulder with a Blue Satin Off-the-Shoulder Top

Calling all neutral lovers: If you tend to gravitate toward black or white, this is your sign to venture out of your comfort zone and embrace a cool-toned blue. A luxe material like a silky satin is ideal for a romantic evening, thanks to its lustrous finish and soft feel, and you may be surprised to discover that an ocean hue can speak to your character. Blue can convey that you’re affectionate, warm and a good communicator, according to cognitive psychologist Hailey van Braam for Color Psychology. Sounds to us like some good partner traits and dating green flags.

date night outfit ideas Sheer
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19. Risk It All in Sheer

Dare to show some skin? A touch of sheer detailing can feel fresh and coquettish over a few rounds of martinis. You can choose to make it as revealing (or conservative) as you please, from a faint peekaboo blouse to see-through tulle addition under a mini skirt to a lacy appliqué fabric on a dress.

date night outfit ideas Knee-High Boots with Tights and a Mini
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20. Combine Knee-High Boots with Tights and a Mini

You know what they say, “look good, feel good,” so let’s break out your favorite pair of sturdy knee-high boots and tights for your evening ahead. Better yet, pair it with a mini skirt, short or dress. After all, what’s the point of wearing tights if you can’t show them off? This will draw the eye towards your legs and create the appearance of a long and lean silhouette.

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Associate Fashion Commerce Editor

Stephanie Meraz is PureWow’s Associate Fashion Commerce Editor. Stephanie is a natural savant in the fashion, beauty, and dating & relationships beats. She has over 22+ years...

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