The Prettiest Dresses For Valentine’s Day For Every Kind Of Date

Raise your hand if you have ever felt personally victimized by someone claiming that Valentine’s Day is just a Hallmark holiday.

By Anna Hartman3 min read
Breeana Wrap Mini Dress in Dusty Pink

Of course, it’s an excellent excuse for brands to capitalize on special sales and themed gift ideas. But, what I never got was: why is anyone complaining about this? I, for one, love a good sale, and I’m definitely not mad about treating myself to a cute pink dress and heart-shaped chocolate while simultaneously showing my husband how much I appreciate him. 

Valentine’s Day only comes once a year, and although we should be showing our love to the special people in our lives every day, realistically sometimes life gets in the way. This holiday serves as a much-needed reminder to hit the “pause” button, write a thoughtful note, and spend quality time with someone you love. 

Even if you’re solo this Valentine’s Day, I think it can be so special to take a moment to treat yourself to something you’ve been eyeing (a stunning new outfit or a fancy spa treatment, perhaps), meet up with your girlfriends, or take a risk and head out on a first date (at worst, you have a good story to share later; at best, you meet the love of your life). 

Since you did click on this article though, I think it’s fair to assume that you’re just as jazzed about Valentine’s Day as I am, so let’s get started on what you should wear. As someone who would choose to wear a pretty dress all day every day if she could (hi, it me), I have to say that I feel as if you’ve come to the right source. 

No matter what your plans are this Valentine’s (or Galentine’s) Day, I’ve got you covered with the prettiest dress options for any occasion. 

For a Romantic Dinner Date

Forego the outfit your partner has seen numerous times and slip into a dress that has a sultry edge to add an element of surprise this Valentine’s Day. For a romantic setting like a fancy restaurant, I love choosing a dress that has sexy details like a cut-out, a high slit in the leg, or lace frills. Not only will you get to indulge in a delicious meal, but you can use this occasion to show off your more glamorous side without feeling out of place.

Hello Molly Bright Horizons Dress, $75

Revolve Mary Kate Mini Dress, $228

For a Casual Day Date

Some of my most memorable dates with my husband happened in the daytime. Whether it’s a well thought out scavenger hunt around the city or a spontaneous park picnic and matinee showing, a casual day date is no reason to feel frumpy. Throw on a flowy dress with boots or flats and add a daytime accessory like a waist belt or wide-brimmed hat to look perfectly chic. 

Red Dress Love Always Ivory Floral Print Midi Dress, $58

Revolve Feeling Groovy Maxi Dress, $168

Showpo Levana Dress in Black, $60 

For a Date Night In

Who says you can’t get dolled up for a date night at home? New parents (and, really, parents in general) know the drill. As a mama to a 10-month-old baby boy, I’ll be embracing Valentine’s Day at home this year and making it as intimate as possible. Each of these dress options has an element of comfort to them: from a silky wrap dress to a cozy knit combo to a flowy maxi to dance around the kitchen barefoot in. 

Showpo Breeana Wrap Mini Dress in Dusty Pink, $70

Daily Practice by Anthropologie Slim V-Neck Dress Set, $90

Red Dress Heat Of The Moment Blush Floral Print Maxi Dress, $62

For a First Date

First impressions can truly make or break a new relationship. That’s why it’s imperative to put a little extra thought and effort into choosing an outfit when meeting a crush. In my opinion, the ideal dress for a first date is a simple, but form-fitting midi dress. You’ll look incredible without baring it all or showing that you tried too hard.

Showpo Coming For You Mesh Midi Dress, $70

Revolve Sylvie Sleeveless Midi Dress, $113

Hello Molly Love Rider Midi Dress, $89

For a Galentine’s Happy Hour

Whether you’re heading to a restaurant for a couple of cocktails or meeting up at your girlfriend's house for a romcom movie marathon on the couch, use Galentine’s Day as an excuse to wear something a bit over the top. Bonus points if you text the ladies and make a theme of it: wine and chocolate pairing party, single in the city (based on SATC), sip and paint, or fondue night are some of my favorites. 

Revolve Parliament Dress, $295


Revolve Cassandra Sweater Dress, $74

Showpo Lydia Jacquard Puff Sleeve Mini Dress in Pink, $89

Closing Thoughts

With so few occasions to get dolled up these days, use this Valentine’s Day as an opportunity to embrace feminine silhouettes, delicate patterns, and shades of pink and red. No matter what your plans are or who you’ll be celebrating with, make it a holiday to remember with a pretty new dress.

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