Dressing For Love: 7 Date Night Outfits For Every Occasion

Whether it’s movie night, a springtime hike, or a fancy dinner, we’ve got a look you’ll love.

April 21, 2018
img Dressing For Love

Disclaimer: Just so you know, if you order an item through one of our posts, we may get a small share of the sale.

Maybe it’s not quite love at first sight, but you both swiped right and decided to meet up Friday night. You’re going out to that swanky Italian place that just opened up downtown—it’s bound to be an interesting experience and could lead to something more. You’re buzzing with excitement over the possibilities.

But you take a look a look at your closet and dread sets in: What are you supposed to wear to impress your date?

You probably want something flattering (that doesn’t look like you tried too hard). You’re looking for something that’s sexy yet comfortable and that won’t reveal when you’ve had a few ravioli too many. You hope to find the perfect balance between trendy and classic. And of course, the date night outfit has to come in that perfect shade to complement your baby blues. But where do you begin putting together a look?

HealthyWay’s got you covered. We’ve put together a guide to help you find the perfect date night outfits for every occasion, whether you’ll be slurping spaghetti, bouncing around the best cocktail bars in the city, or doing something a little more adventurous. (Trust us: You can find love at the indoor rock climbing gym.)

Here’s what to wear on your next date.

Date Night Outfits for When You’re Dressing for Love

Dressing for love is an art, rather than a science. There are no hard and fast rules for choosing a date night outfit that will make your sweetheart swoon. More than anything, you want to create a look that’s true to who you are.

If the date night outfit makes you feel amazing about yourself, you’re golden. Confidence is the most beautiful quality in a partner. Do you love mixing and matching prints? Throw on your splashiest skirt and strut with pride. Maybe you’re more of a minimalist who feels gorgeous in classic cuts. Go for a monochrome look that accentuates your silhouette.

Beyond dressing authentically, however, there are other factors to consider. What’s the weather forecast? What’s the planned activity? What’s the vibe of the venue? You want to find a date outfit that will keep you comfortable, whether you’re hiking on a chilly spring day or standing for a few hours as your favorite band jams on stage. It’s always a good idea to grab a sweater (doesn’t every restaurant have a draft?), wear shoes that don’t pinch (at least not too much!), and make sure your accessories don’t get in the way.

One last tip: Always try sitting down in your date night outfit before you go out. It could shift in ways you wouldn’t expect, and you may want to make a quick swap to something that hits you in all the right places, whether you wind up sitting or standing.

First Date at a Casual Pizza Joint

Nothing takes the edge off a first date quite like agreeing to go somewhere friendly and chill. But what’s the right date night outfit for a casual dinner? Try that classic early 2000s favorite: jeans and a nice top.

Madewell’s curvy high-rise skinny jeans in black sea hug the body in all the right places. They come in dozens of sizes, including inseams specifically for short, tall, and “taller” women. The raw hems and hand-ripped knees will show that you’re on point with 2018 fashion trends.

A sheer top elevates the overall look into a flirty ensemble. BB Dakota’s lacy short-sleeve crew neck top or Free People’s v-neck muscle tank would look sharp with high-waisted skinnies—and offer enough wiggle room for you to nervously scarf down too much pepperoni if it comes to that.

Date night outfits don’t always require heels. Keep it casual with a pair of cute flats, like sustainable footwear brand Rothy’s black flats with a pointed toe, which are made from recycled bottles, or Sam Edelman’s on-trend woven mule.

The lace top should be the most eye-catching element of your casual date night outfit. Simplify your accessories with some gold bangles, like these recycled brass stacking cuffs from SOKO, handmade by Kenyan artisans. Stash your keys, phone, wallet, and lipstick in a chic black bag, like this eco-friendly clutch from Matt & Nat.

Get The Look:

Luxe Date With Your Long-Term Partner

We tend to settle in and get cozy when we’re in a long-term relationship. But your partner wants to splurge on a five-course meal at a Michelin-starred restaurant, and you’ve got to dress the part. What’s the best date night outfit to wear when you want to dazzle your partner (who has already seen you in everything)?

This is the perfect time to try something bold and eye catching, like a jumpsuit. Yumi Kim’s known for its rompers and jumpsuits. The brand’s silk floral romper radiates the right amount of romance for a summer date night outfit. A long-sleeve midi dress in a pretty floral print is a smart alternative to wear when the weather’s cooler, and the draped wrap style will hang nicely on a variety of body shapes. If prints aren’t your thing, check out this solid black jumpsuit from Amour Vert. The sustainably made garment features hypoallergenic silk that can be worn year round and is colored with only nontoxic dyes.

Choosing the right shoe is critical when wearing a jumpsuit. A heel gives you a lift that will turn heads. Sam Edelman’s ankle strap block-heel pump in nude creates lean lines and elongates your legs. Or we love these block heel sandals from ABLE, which employs women living in poverty around the world. The store only offers cruelty-free items, so you’ll feel good knowing no animals were harmed in the making of your heels.

Tie your hair back in a low bun or flirty braid and wear an understated yet elegant necklace like the Cascade Lariat from ABLE to show off your neckline. Stash all your essentials in a statement-making crossbody bag, such as this mini chain saddle bag or a sleek modern clutch from Urban Originals. The overall date night outfit will look both sexy and sophisticated—perfect for wowing your long-term sweetheart.

Get The Look:

Rock Concert With Someone You’re Getting to Know

It’s been a few months and you’re really enjoying spending time with this person. You noticed their favorite band is playing a live show in a couple weeks and you scored tickets! This occasion calls for a date night outfit with an edgy rocker vibe that will make you the star of the show.

Let’s work from the top down. A muscle tank with graphic vintage elements is a nice throwback to the rocker look from the 1970s, especially if you knot the bottom. This sequin tank from Express has elongated arm holes that will play peekaboo with colorful a lacy bralette (this one from Amazon comes in a ton of colors). Alternatively, create a rocker chic look with this distressed tank from Alternative Apparel and this classic collar necklace from Nisolo. For a more eclectic vibe, add a layered-look necklace and a stack of rings to finish off your look.

Keep the ’70s vibes flowing with high-waisted wide leg jeans from sustainable fashion giant Reformation, which cleans a thousand gallons of water for every pair sold. Lucky Brand offers a pair of tomboy-style jeans with a similar cool factor. If your concert date is outside during warmer months you might opt for a cool pair of cut-offs like this one from AGOLDE.

A date night outfit for a rock concert demands a shoe that’s both stylish and comfortable (you’ll be standing for a few hours). ASOS has the perfect pair of studded sandals with a chunky block heel for comfort and stability. But if any sort of heel will stifle your dancing, choose a metallic sneaker instead for a date night look that’s both fun and funky. These shiny sneakers from Veja are perfect for grooving all night, and they’re made from eco-friendly materials.

You’ll want to keep your hands free to hold a drink and shoot pics of the band, so try to take advantage of your pockets to hold your lipstick, phone, and wallet. If you have to carry a bag with this date night outfit, choose a small shoulder bag that features fun details. Urban Originals vegan leather embossed shoulder bag should do the trick.

Get The Look:

Indoor Rock Climbing on a Third Date

Active dates are one of the best ways to get to know your new beau a little better. If you’re heading to the indoor rock climbing gym, you’ll need to find a date outfit that allows for ample range of motion but won’t hide your figure or compromise your style.

Sustainable activewear brand ADAY’s leggings are stretchy, sweat-wicking, and supportive. These leggings will move with your body as you climb to the top of the rock wall, and they have a handy pocket for your phone and keys. Outdoor Voice’s Slashback Crop Top will keep you dry and supported even as you work up a sweat. Throw on a cool bomber jacket, slip into some fun slides or sneakers, grab a cute gym-friendly bag, and you’ll be ready to go.

For makeup, you’ll want to keep it more natural, but tarte offers a great gym essentials kit for a natural but active-date-ready look.

Socks are usually an afterthought for date night outfits, but you’ll need to pick a nice thin pair to slide on with your rock climbing shoes. Bombas offers a four-pack of no show socks in neutral colors with the classic bumblebee logo, and they’re a great conversation starter while you’re gearing up to climb: For every pair sold, the brand gives a pair of socks (one of the most requested items at homeless shelters) to someone in need. If you thought your heart could only be worn on your sleeve, think again!

Get The Look:

Going on a Hike With Your Crush

A friend that you’ve been crushing on for a while has invited you to take a hike. You’re both friendly and familiar, but you’re trying to take things to the next level. What should you wear?

Layers are your best friend here: You’ll want to bundle up to fight off the chill of the morning with the ability to strip off heavier garments as you warm up on the hike. Think leggings, tank top, sweatshirt, and maybe a hat and scarf, depending on the weather.

Outdoor Voice’s Hi-Rise 7/8 Legging are a great pick for a hiking date legging. The sweat-wicking fabric, four-way stretch, and universally flattering fit that sculpts, lifts, and tones make them perfect for exploring the great outdoors. On top, start with this strappy two-in-one tank from lululemon, then layer on something that offers some protection, like Athleta’s sustainably-made Vitamin Sea Jacket. This jacket offers UPF 50+ coverage and is made from post-consumer plastic bottles, meaning it’s not only doing good for you—it’s helping the environment as well.

Finally, if the weather necessitates additional layers, add a vest for a date outfit that’s fit for the forest. This lightweight water-resistant packable down vest is a great choice that can be rolled up, packed neatly into the included carrying bag, and stored in your backpack if you get too warm. Toss your hair into a ponytail, throw on your favorite baseball cap, and get ready to hit the trail (hopefully hand-in-hand with your hiking buddy!).

Get The Look:

Date Night Outfits for Formal Events

Every once in awhile, you’ll get an invite to go somewhere truly extravagant, like a charity gala, the opera, or the ballet. You’ll need a date night outfit that will turn heads as soon as you walk in the door.

You can’t go wrong with a little black dress, but try to find one that has some attitude and isn’t too short. This body-con midi dress from Nordstrom has a faux wrap look with ruching at the sides that accentuates the body-con fit and is flattering for your waistline. With this look, you can really dress it up with glam statement jewelry like these Miguel Ases handmade earrings, which are very lightweight and comfortable. Polish off this sleek look with a dramatic smokey eye using Kat Von D’s Shade + Light Eye Contour Palette.

For a head-turning color in a silhouette that will wow, go for Reformation’s Callalily dress. With a deep v-neck, an open back, and a high slit, you’ll be turning heads in this date night outfit.

If you’re looking for a truly stunning date night outfit for a formal event, Monsoon’s embellished maxi dress exudes old-school Hollywood glamour. The intricate beadwork is handmade not only to give each dress a unique look, but also to help sustain traditional craftsmanship techniques in Asia.

Carry everything you need in an acrylic clutch that brings an element of surprise to an otherwise classic look. This Cult Gaia clutch has a mod appeal. If you’re looking for something a little more traditional, Gigi New York offers a variety of clutches that can be used both for day and evening, like this Stella Fold-Over Clutch which has a conveniently detachable crossbody strap.

Sexy stilettos are a must for fancy date night outfits. Check Beyond Skin for high-end, cruelty-free footwear designs, like these t-strap stiletto heels. Or try Sam Edelman’s Ariella Ankle Strap Sandal for a moderately priced, versatile go-to.

Get The Look:

Date Night Outfits for When You Just Want to Netflix and Chill

Date night doesn’t always mean going out: Sometimes snuggling up with your SO on the couch in front of a few flicks can be more romantic than anything else. A chill night is no excuse to look frumpy, though.

Date night outfits for movies at home should create an alluring look that allows you to sprawl out and snuggle up comfortably. The silk sleep set from Everlane is a casual date night outfit with a cute cut your guy will love. Conversely, you could slip on these cropped joggers from Anthropologie and a super soft but stylish sweatshirt from Athleta.

And when it comes to Netflix and chill, what you wear underneath matters just as much as what’s on top. Choose a matching bra and panty set that makes you feel like a goddess. The Secret Life of Hummingbirds lingerie collection from Naja gives you a variety of flattering styles, all of which are made by single mothers or women heads of households. If supporting other women isn’t sexy, we’re not sure what is.

Get The Look:

ABOUT THE AUTHOR