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30 Stunning Date-Night Dresses Worthy Of Valentine's Day

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It's no news that dressing up for date night can be absolute mayhem. One minute you're cruising through your closet, excited for the evening, and the next, you've blacked out, only to wake and find the topography of your room has entirely transformed — the once freshly Swiffered floors are replaced by a mountain range of discarded clothing, and yet you've made no progress on what to wear, with T-30 to spare (yikes).

Well, let's not let that stressful scenario ever happen again. Getting ready should be mindless, but less of a total zone out and more of an, Oh, but of course I'll just throw that on. How easy. In the slideshow ahead, we've rounded up 30 dresses that will not only keep you sane (and keep your place from becoming the Himalayas of clothing), but will also have you exuding some good old-fashioned confidence. Click through to find the next fool-proof, flattering dress for your upcoming date night.


Keep this number around for every season: Wintertime? Pop a black turtleneck underneath. Still chilly in spring? Wear it over a sheer black T-shirt or under your go-to moto jacket.

ASOS White Twill Satin Mini Dress with Strap Detail, $128.30, available at ASOS.

Okay, this is the best way to fully cover up and kill the date-night game. Hot damn.

Ann-Sofie Back Ribbed Lamé Turtleneck Dress, $280, available at Opening Ceremony.

Wow everyone in the room, not just your date.

Karla Spetic Juliette Contrasts Dress, $481.48, available at Karla Spetic.

Don't let this dress trick you: The sheer lacy top outshines the sweetness.

Valentino
Lace Top Dress, $4,290, available at Farfetch.

If you're going LBD, try for a silhouette that's a little more unexpected. We are feeling this tux-inspired dress.

Nasty Gal Jackie Off-The-Shoulder Mini Tux Dress, $88, available at Nasty Gal.

When off-the-shoulder meets body-con, the result is a whole lot of yes.

Self-Portrait Off Shoulder Flared Dress, $357, available at Self-Portrait.

This dress would even look good with your chunky Doc Martins.

Reformation Eleanor Dress, $248, available at Reformation.

Simple and clean does the trick.

Alexander Wang Tie Detail Tunic Dress, $742.67, available at Harrods.

A shirtdress is perfect to throw on when you're feeling lazy. It takes zero effort, plus you'll still look put-together.

Ganni Clark Dress, $165.65, available at Ganni.

Dress this up for your date, dress it down for daytime.

Zara Lace Dress, $169, available at Zara.

Bell sleeves and a velvet texture make this LBD feel more unique.

Motel Lou Babydoll Dress, $31, available at Motel.

An unexpected color that's totally worth a try, hands down.

C/meo Collective Perfect Lie Dress, $170, available at Need Supply Co.

If you're thinking of going for something bold and pink, choose a sleek, less girly silhouette. The baby fringe and white buttons make this A-line number a rad choice.

Edun Frayed Satin Dress, $884, available at MatchesFashion.

Sweater dresses can be tricky to pull off, since the material is oftentimes so thick. An off-the-shoulder iteration, however, levels everything out, and turns this knitwear piece from frumpy to sexy.

Forever 21 Plus Size Marled Off-The-Shoulder Dress, $22.90 $15.99, available at Forever 21.

Wear this again in spring with jeans underneath.

J.O.A. Button Front Mini Dress, $73, available at Shopbop.

Make a strapless dress feel less bridal by accessorizing with a choker.

Ty-Lr The Invader Dress, $295, available at Ty-Lr.

An intentional "Oops, my strap slipped off my shoulder" that looks unintentional.

Third Form Bracket Dress, $289, available at Third Form.

Casual date night? Take away the hassle of finding the perfect tee to wear under that tank dress.

Topshop Two in One T-shirt Midi Dress, $40, available at Topshop.

We can't believe this dress is only $32. Spend the rest of your money on a good bottle of wine, instead.

Forever 21 Tie-front Halter Dress, $32.90, available at Forever 21.

There's a right way to do red on date night, and this is it.

Lucca Couture Eda Satin Mock Neck Dress, $74, available at Pacsun.

The beauty of this dress is its versatility: Wear it over pants (as seen in the photo), by itself, with a T-shirt underneath, or layered with a turtleneck or button-down. This piece captures the shapeshifting essence we love about LBDs.

H&M V-neck Dress, $59.99, available at H&M.

Thinking of something body-con? Choose an option with a longer hemline and interesting neckline.

Elizabeth and James Riza Cutout Stretch-Ponte Halterneck Dress, $385, available at Net-a-Porter.

When your skirt and shirt combos just aren't cutting it, grab this look instead. You get the two-piece feel, but don't have to think twice about whether they match.

Pixie Market Sweater Ruffle Two Piece Dress, $86, available at Pixie Market.

The most effortless metallic dress, ever. Throw on nearly any shoe and your look is ready to rumble.

FRS Silver Silk Evening Dress with Back Details, $212 $180.20, available at Front Row Shop.

Surprise! This open-back detail gives a simple shift a twist.

& Other Stories Open Back Dress, $115, available at & Other Stories.

Sultry and super-soft to touch? This sounds like a V-Day winner.

Svilu Crushed Velvet Red Tank Dress, $474.36 $355.38, available at The-Acey.

For the Coachella couple, grab a flirty, boho-inspired frock.

Free People Jasmine Embroidered Dress, $148, available at Free People.

A lesson in looking sexy without showing tons of skin.

Loéil Leroy Dress, $73, available at Loéil.

You can't help but feel like you're getting two for the price of one with this dress. Every time you're out, take pics exclusively on one side.

Harbison Red and Black Color Blocked Dress, $720, available at 151Luwolt.

The '70s? Present and accounted for.

Staud The Strada Dress, $255 $204, available at Staud.



Like what you see? How about some more R29 goodness, right here?

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