51 Date Night Dresses You’d Look Stunning in This Valentine’s Day

Lindsey Lanquist
51 Date Night Dresses You’d Look Stunning in This Valentine’s Day
Photo: Allison Kahler.

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It’s officially mid-January, which means it’s definitely time to start thinking about Valentine’s Day. (Don’t @ me—Valentine’s Day reservations fill up fast.) In the next month, you need to lock down a few things: where your Valentine’s Day date is going to be, what you’re going to get your boo (or boos, if you’re celebrating Galentine’s Day) and of course, what date night dress you’re going to wear. The latter is an oft-overlooked (but crucial!!) part of the Valentine’s Day experience; you want to look and feel your best on the sexiest night of the year, and nothing breeds confidence like a seriously cute Valentine’s Day date night dress.

What makes this process exciting is that there’s no single right answer for what to wear on Valentine’s Day. Some may find their sartorial soul mate in a classically sexy form-fitting dress, while others might turn to a flowy floral maxi dress for all the answers—or a flouncy party dress, or an edgy shift dress, or a wrap midi. The options are endless, because the ways we express ourselves are endless. And as laughably cliche as the adage may sound, we’re all at our hottest when we’re being ourselves. (Eye-roll away, but you know the last thing you want is to show up to date night wearing something that makes you feel awkward, uncomfortable or generally untrue to your aesthetic.)

Thankfully, the online shopping-verse is so full of Valentine’s Day date night dresses that you’re sure to find at least one you love. Honestly, you’ll probably find a bunch—which is a good problem to have. Just stock up on ’em all and dole ’em out for date nights to come.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Whistles Limited Ari Hibiscus Midi Dress, $315 at ASOS

A Valentine’s Day dress so chic you could wear it to work on February 15 without anyone realizing you were walk-of-shaming.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Vila Pleated Metallic Knot Midi Dress, $64 at ASOS

Honestly tempted to buy this and wear it on my Valentine’s date.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Metallic Satin Midi Dress, $148 at & Other Stories

Because pink and red aren’t your only color options for the calendar’s most romantic holiday.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Kimono-Sleeve Midi Dress, $60 at ASOS

A Valentine’s Day dress you can definitely take from work to cocktail hour.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Scatter Sequin Knot-Front Kimono Midi Dress, $119 at ASOS

It’s your Valentine’s Day—you can sparkle if you want to.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

WAYF Arden Lace-Up Dress, $89.60 at Shopbop

Particularly fit for those celebrating February 14 in warmer climates.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

L’Academie the Judy Midi Dress, $188 at Revolve

Distinctly sexy without feeling overstated—and fit for re-wear at parties, over the holidays and on date nights for years to come.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Cluster Drop Bead Cami Slip Midi Dress, $86 at ASOS

Because form-fitting simply isn’t the only way to look hot.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Marieta Applique Dress, $338 at Free People

Definitely the funnest thing you could wear on your Valentine’s Day date.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Blue Bird Sequin Embroidered Maxi Dress, $539 at Free People

A black sequin dress might sound like an over-the-top thing to wear on a date, but when the dress looks this sleek, it’s begging to be taken for a date night spin.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Majorelle Lulu Dress, $158 at Revolve

An absolute classic (and a silhouette that’s worth having in your closet, Valentine’s Day or not).

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Fashion union Wrap-Front Maxi Dress, $36 at ASOS

A super romantic (and understatedly hot) take on the Valentine’s Day dress—and one you can definitely get away with wearing to weddings, backyard barbecues and summer parties.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Shoshanna Feona Lace Dress, $299.95 at Anthropologie

Because nothing says Valentine’s Day like a figure-hugging dress rendered in dark red lace.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Chevron Plisse Maxi Dress, $72 at ASOS

Luxe, sophisticated and so soft your date won’t be able to resist touching it.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Shona Joy Cocktail Draped Dress, $279 at Revolve

Probably the most glam look on this list. But again, it’s Valentine’s Day—this is your excuse to look hot AF, even if that means being extra AF, too.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Lace Shift Mini Dress, $56 at ASOS

Practically begging to be paired with that red lipstick you rarely break out.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Curve Metallic Plisse Midi Dress, $72 at ASOS

Equal parts comfortable and glamorous—what’s not to love?

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Myle Maxi Dress, $219.95 at Anthropologie

Winter maxi dresses are definitely a thing—and they’re sexy as hell.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

ML Monique Lhuillier Paris Sequin Dress, $495 at Anthropologie

If you’re going to a fancy-ass dinner, or a fancy-ass bar, or a fancy-ass anything, you can get away with wearing this. Trust me.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Leather Wrap Mini Dress, $420 at Topshop

Is anything more classically sexy than a black leather dress?

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Carson Tiered Dress, $396 at Anthropologie

Because “sexy” and “fun” are far from mutually exclusive.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Black Halo Micah Sheath Dress, $345 at Anthropologie

This dress screams Valentine’s Day—and it’d look great on you.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

High-Shine Satin Midi Slip Dress, $64 at ASOS

Slip dresses are no-fail Valentine’s Day options, regardless of shade.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Riella Strapless Jumpsuit, $210 at Anthropologie

Oh yeah, jumpsuits are totally on the menu.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Michael Costello x Revolve Kianna Dress, $178 at Revolve

A dress that’s sure to leave your date wanting more all night long.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Ganni Tilden Sash Dress, $90 at Shopbop

Because Valentine’s Day is a cute holiday, and nothing says “cute” like flowers and tulle.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Off-Shoulder Wrap Midi Dress, $72 at ASOS

A seriously luxe dress rendered in a seriously luxe color—need I say more?

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

About Us Eliana Flare Dress, $68 at Revolve

Impossible to go wrong with navy velvet—especially navy velvet rendered in such a universally flattering silhouette.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

ML Monique Lhuillier Eva Lace Dress, $495 at Anthropologie

Form-fitting without actually being figure-hugging, this lace pencil dress offers the perfect blend of sophistication and sex appeal.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Shoshanna Adali Dress, $398 at Anthropologie

Consider Valentine’s Day your excuse to wear the hottest pink you can find.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Tall Midi Pencil Dress, $111 at ASOS

Because gold is an out-of-the-box choice sure to keep all eyes on you all night long. (Not that all eyes wouldn’t have been on you anyway, of course.)

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Stripe Belted Midi Dress, $50 at Topshop

Sweater dresses are super underrated in the sex appeal department—and they’re weather-friendly.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Ruffle Wrap Dress, $65 at & Other Stories

This silhouette is an absolute classic.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Bardot Lucy Lace Dress, $159 at Revolve

This sleek blush dress leaves just enough to the imagination.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Shoshanna Hollybrooke Sequin Dress, $385 at Anthropologie

A date night dress you can rewear anywhere.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Michael Costello x Revolve Atienne Dress, $378 at Revolve

Semi-transparent lace offers an ideal blend of romance and sex appeal—and sky blue’s a super underrated color to wear on Valentine’s Day.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Michael Costello x Revolve Marlene Dress, $178 at Revolve

I mean, who doesn’t love a millennial pink mini?

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Pleated Wrap Floral Maxi Dress, $72 at ASOS

I didn’t know how much I needed a floral maxi until I saw this ASOS gown.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Needle & Thread Sequin Embellished Cami Midi Dress, $419 at ASOS

Simultaneously romantic and party-worthy, this dress is perfect for whatever the night has in store.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Michael Costello x Revolve Justin Gown, $238 at Revolve

I own this dress in black, and it’s exactly as sexy as it looks.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Dixie Metallic Jumpsuit, $249 at Anthropologie

Because wearing a floor-length silver jumpsuit on Valentine’s Day is a total power move.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

House of Harlow 1960 x Revolve Ira Midi Dress, $119 at Revolve

Sleek, luxe and a little edgy, this midi offers the best of all kinds of worlds.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Satin Kimono Maxi Dress, $30.50 at ASOS

I mean, why not look like an absolute goddess?

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Shoshanna Bativa Mini Dress, $455 at Anthropologie

This dress is absolutely someone’s Valentine’s Day style soul mate.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Cleobella Amarylis Embroidered Maxi Dress, $245 at ASOS

Black is totally on the table—especially if it’s adorned with dainty floral details.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Lovers + Friends Tinley Midi Dress, $278 at Revolve

I mean, need I even justify this sexy LRD?

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Pleated Maxi Kimono Dress, $60 at ASOS

Because sometimes all you need is an understatedly sexy black maxi.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Cherie Bodycon Mini Dress, $209 at Free People

So cute you’ll be looking for excuses to wear it for months on end.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Kimono Pleated Midi Dress, $56 at ASOS

Not into red or pink? Maroon offers a way into the Valentine’s Day palette without forcing you into too-bright territory.

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

Michael Costello x Revolve Kellianne Gown, $278 at Revolve

I mean, when you have an opportunity to wear a floor-length, deep-V, high-slit, fire-engine red lace gown, you take it, right?

STYLECASTER | 51 Date Night Dresses You'd Look Stunning in This Valentine's Day

House of Harlow 1960 x Revolve Sabrina Dress, $298 at Revolve

Just think of all the statement accessories you could pair this classic dress with.

 

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