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

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.

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.

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.

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.

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.

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.

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.)

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.

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.

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.

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.

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.

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.

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).

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.

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.

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.

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.

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.

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.