What to Wear on Valentine’s Day

‘Tis the season for Lindor truffles, heart-shaped candies, and rose bouquets. Even if you’re single, it’s relatively easy to feel the Valentine’s day spirit. Romance is in the air, the aura of love has never been brighter—and I swear, it’s the only holiday that offers the best colors. 

Red and pink isn’t everybody’s cup of tea, but I think we can all agree they serve a charming visual cue. If you’re lucky enough to have a plus one, you’re probably brainstorming outfit ideas to wear on that special day. 

I know Valentine’s Day often gets a bad rep for being overly sexualized and cheesy. From body-con gowns to penguin tuxedos, pop culture often exaggerates our image of romance. It’s time to take the power back and make things more realistic. 

If you’re in need of outfit inspo, we’ll show you what to wear on Valentine’s Day. From simplistic and sweet to mysterious and casual, you can take care knowing we’ve got fits for everyone. 

What is Valentine’s Day?

In short, Valentine’s Day is an annual holiday that happens on February 14. Once a year, people show their gratitude and love to their friends, family, and significant others. Its importance is often exaggerated by the media, most notably advertisements. 

You can express your intentions through cards, chocolate, flower bouquets, and jewelry—but some old-time celebrants resort to more sentimental gifts instead of a corporate schmuck. It’s up to you how you want to celebrate the day of unconditional love. 

History of Valentine’s Day

Pink and red fanatics, we thought it best to imbue you with some historical knowledge about February 14. Who knows? Maybe it’ll provide inspo on what to wear on Valentine’s Day. 

Most celebrants associate Valentine as a catholic saint. Funnily enough, the church recognizes three patrons that fall under this name. One served under the heady Emperor Claudius, who outlawed marriage for young men, with the logic being that singles made better soldiers. 

Valentine disagreed, and being a priest—he performed marriages for lovers in secrecy. When Claudius found out, Valentine was executed. The other martyr who goes by the same name, Saint Valentine of Terni, also served under the Roman emperor and quickly met the same fate. 

The origin story behind Valentine’s Day is still in murky waters. For instance, Valentine wasn’t a cupid in priest clothes but rather a Christian sympathizer who helped believers escape Roman prisons.

Others tell a tale of a love-sick jailbird who had an eye for the warden’s daughter. Either way, the stories seem to depict a man and his selfless actions of love. 

Early celebrants of Valentine’s Day believe that the holiday was made to replace the pagan festivity Lupercalia. Due to the rise of Christianity, the tradition was soon outlawed by religious officials. Valentine’s Day wasn’t associated with love until the Middle Ages when heartfelt cards were exchanged between lovers.

What to Wear on Valentine’s Day

The best way to tackle the ‘what to wear to Valentine’s Day’ question is to address what not to wear. Romance is the opposite of laziness. You don’t want to show up to dinner in sweatpants and sneakers. 

February 14th posits a unique opportunity to don your best clothes, whether that be an expensive dress, a fancy suit, or your most expensive pair of Oxfords. Take the day as a sign to look like a 2.0 version of yourself!

For those in need of ideas, we’ll share some Valentine’s day outfits worth considering. 

12 Outfit Ideas for Valentine’s Day

Pink is always an acceptable color to wear, and it’s considered absolutely necessary during the day of love. If you’re in need of a cute Valentine’s outfit, we suggest hamming things up by going all blush. 

This ensemble comes with a cozy knit cardigan, a pencil skirt, a red graphic tee, polka-dot socks, and matching heels. You don’t have to dye your hair pink, but we do suggest adding a cute heart-shaped bag as a complimentary piece. 

I get it; not all of us are keen on sugar, spice, and everything nice—which is why we decided to share a casual Valentine’s day outfit for our second example. In this instance, a pop of red is absolutely necessary to help unearth the blush tones in your skin. 

To keep things neutral, a chunky cable-knit sweater, jeans, and a pair of pointed-toe booties do wonders in emphasizing the vibrancy of the coat. Hair-wise, we recommend something flirty and fun, such as a subtle wavy moment. 

If wine-tasting in the Italian countryside sounds like your ideal Valentine’s date idea, it’s best to don the romantic cottage-core look. Obviously, not all of us are blessed with warm weather on February 14th, but if you’re lucky to score a plane ticket overseas, this is the outfit to go for. 

Featuring a jaw-dropping floral gown with a front tie to help accentuate the waist, the rattan bag, and the strappy heels help to elevate the ensemble. Honestly, all that’s missing is a champagne glass. 

On the hunt for some sexy Valentine’s day looks? Well, there’s nothing wrong with opting for the classic lbd. If you’re not familiar with the lingo, it basically means ‘little black dress.’ It’s important to find a fit that conforms to your body shape. 

Going for silks and satins is usually the best bet, as it’s prone to curve and drape over your best assets. To pair with the look, a set of strappy heels, simplistic jewelry, and a matching clutch are a must-have. 

If you’re hosting a Galentine’s day get-together, perhaps it’s best to leave that sexy slip dress for upcoming dates. We suggest keeping things super casual by donning a heart sweater and high-waisted white pants. 

It’s an adorable look for low-key events, such as baking cookies with your friends, doing arts and crafts, or having brunch together on February 14th. For those searching for ‘what to wear on Valentine’s Day with your significant other,’ this is the look to go for. 

Not keen on wearing heels? No worries, we hear you loud and clear in this ‘what to wear on Valentine’s Day’ article. For those gearing up for hourly walks at the park or art museum, we recommend wearing a pair of clean kicks with a frilly summer dress. 

Yes, tennis shoes are usually a no-no during February 14th, but it’s forgivable if you opt for something more romantic over top. The floral print of the gown paired with the elegant handbag helps to imbue those lovey-dovey vibes. 

Romance is not exclusively defined by frilly pink dresses and stiletto heels. At the end of the day, it’s all about putting effort into what you wear. Take, for instance, this pant-suit outfit, which features Kendall Jenner in a super-flattering striped set.

Composed with trousers, a white, a well-fitted blazer, and tennis shoes, it’s the perfect ensemble if you’re not in the mood to sport a skirt. The crossbody bag is completely optional, but we suggest carrying a mini clutch for a more elegant take. 

Picture this: you’re a New York City girl who frequents vintage bookstores and local cafes. Caught in the fast-moving pace of a metropolis that never sleeps, you yearn to find little pockets of love. 

I know, I basically described a Hallmark movie in its essence, but isn’t that the first thing you think of when you see this outfit? Featuring a red satin midi skirt, a plunge-style long sleeve, and Dr. Marten boots, it’s the ideal ensemble to wear if you want to imbue main character vibes. 

If you’re still in the market for a sexy valentines day outfit, we suggest trying this ensemble on for size. I swear, nothing’s more sultry than a sheer bustier moment. It does wonders in highlighting your curves, ‘girls’, and decolletage. 

While some trendsetters sport it with a dress or a pair of jeans, we recommend keeping things monochrome by donning a matching pant-suit set. Shoes are totally up to you, but how about some strappy white heels for added sophistication?

Not a fan of modern romance? If so, why not take inspiration from Jane Austen, William Blake, and Bridgerton? For those keen on vintage ‘chivalrous’ silhouettes, the puffy poet sleeve can do just the trick. 

Conservative, dramatic, and oh-so-elegant, this top can help imbue that Elizabeth Bennet nightgown vibe from Pride and Prejudice. You’re free to wear a skirt, but we suggest keeping things casual with a pair of jeans. This, ladies and gentlemen, is what to wear on Valentine’s Day if you’re an old-school romantic. 

If you’re a burger and fries type of gal on Valentine’s Day, chances are that you’re not in the mood for floral gowns and satin skirts. But, there should be no reason why you can’t dress up for your boo on February 14th. 

Considered a great mix between super casual and fancy, the slip dress tucked into a pair of jeans combo is the best compromise for V-day. For those unkeen on showing too much skin, you can always layer up with a cozy cardigan. 

Considered an excellent look for study dates and grabbing coffee, this adorable ensemble can help embody those bookish vibes if you’re not a fan of sexy silhouettes. 

I see no reason why brown is exempt as a Valentine’s Day color, as it imbues those rich chocolatey notes that we associate with during the holiday. Comprising an oversized collegiate sweater, a circle skirt, and a matching bag, this is definitely what to wear on Valentine’s Day if you’re feeling super cute. 

What Type of Valentine’s Day Outfits Can You Get?

The ‘what to wear on Valentine’s Day’ debate can easily be remedied by organizing outfits into certain aesthetics. There are typically four kinds of ensembles to fashion during February 14th: sexy, casual, cute, and Galentines.

For those who can’t tell the difference, no worries. We’ll provide a brief summary of each to help increase your styling knowledge. 

  • Sexy: This typically includes body-con silhouettes, thigh-slit dresses, and off-shoulder tops. Basically, you want to show off as much skin and curve as possible. You can achieve this by wearing a slim-fitted gown, a sultry LBD, or a flirtatious peasant blouse. 
  • Casual: If you consider Valentine’s Day as a passing holiday but still feel the obligation to dress up, opting for casual is your safest bet. This includes wearing jeans, sneakers, and oversized sweaters. 
  • Cute: considered the direct opposite of sexy, cute clothes is often a blend of oversized silhouettes, mini skirts, pastel hues, and adorable prints. If you’re thinking of pink sweaters and heart-shaped decals, you’re in the right ballpark. 
  • Galentines: Arguably, this category is considered a mix between casual and cute. It requires a bit of styling know-how, as you want to imbue that relaxed, effortless vibe. In short, you’re dressing for yourself rather than somebody else.

How to Choose The Best Valentine’s Day Outfit

Like any first-date outfit, you need to pay attention to four things: fit, price, quality, and material. You want to make a good impression, so it’s best to find an ensemble that speaks to your character. 

Basically, it’s considered poor taste to don a wrinkly pair of sweatpants to a five-star restaurant. On top of that, it’s also ill-advised to wear a thin, cheaply-made dress to a movie date. 

Celebrants should find a fit that flatters their body shape. Most associate Valentine’s day as a sentimental holiday, but let’s be real—physical looks matter as well. 

Typically, high-quality fabrics such as silks, satins, and organic cotton can help you look like an accomplished trendsetter. Not only does it showcase how well you dress, but it’s also a visual cue that effort was put in on Valentine’s Day. 

Price-wise, V-day is the one day to treat yourself. Whether you’re single or taken, you deserve to feel your absolute best. Of course, budget is worth accounting for, as nobody loves the feeling of a violated wallet.

Hopefully, you’ve got a clear picture of what to wear on Valentine’s Day. 

How to Style Valentine’s Day Outfits

Valentine’s Day is all about romance and drama. Basically, you don’t want to treat February 14th as a casual Friday, as it presents a yearly opportunity to look fancy.

For those who haven’t picked up on some common themes in our ‘what to wear on Valentine’s Day’ lineup, here are some general tips and tricks to keep in mind. 

  • Don’t be afraid to don that body-con dress: if you’re feeling especially confident, why not fashion that stunning LBD you have at the back of your closet? For those not keen on showing too much skin, you can always layer up with something oversized. 
  • Wear minimalistic jewelry: Sexiness and sultriness are best defined through simplicity. You want to be the center of attention and not the bling you wear. 
  • Include some pink or red accents in your fit: Valentine’s Day is full of blush tones. Naturally, it would be a disservice to not include some pinks or rouges to your final look—even if it’s just lipstick. 
  • Wear ‘underwear’ as outerwear: popularized by the Kardashians, you can definitely wear slip dresses and bustiers as part of your fit. 
  • Style around the occasion: if you’re hitting up Five Guys for V-day, perhaps it’s best to leave the stilettos behind. You should always consider the situation before settling on an outfit. 

Fashion Tips to Avoid With Valentine’s Day Outfits

Congrats! You finally know what to wear on Valentine’s Day. But, before you don your desired fit—you should know of some fashion faux pas. Not all ensembles are considered appropriate to wear on February 14th, especially if you’re going on a first date.

Below, we’ve collected some fashion tips to avoid wearing during the day of love. 

  • Athleisure: come on, guys. What part of leggings, sweatpants, and hoodies scream romantic to you? This look only applies on super casual movie dates with your long-term partner. 
  • Flip flops: thongs are definitely appropriate to wear on Valentine’s day, so long as it’s underwear—not sandals. 
  • The full-length ball gown: Unless you’re attending a romantic soiree, there’s no need to don a wedding dress with a train. 
  • Super tight dresses: I know, fashion demands sacrifice—but nothing is more unsexy than being uncomfortable. 
  • Head-to-toe black: let me get this straight: lbds do not fall into this category. Instead, we’re referring to turtlenecks, beanies, jeans, boots—and the whole nine yards. It’s Valentine’s Day, not My Chemical Romance. 

Best Places to Buy Valentine’s Day Outfits

I know; Walmart and Amazon don’t necessarily scream romance. If you’re on the lookout for flirtatious tops, sexy dresses, and fancy pantsuits, we’ll share some stores to consider before the big day arrives:

  • House of CB 
  • Selkie 
  • Reformation 
  • Pretty Little Thing 
  • Indochino 
  • Teuta Matoshi 
  • Lazy Oaf 

Final Thoughts

Valentine’s Day has got to be one of the hardest holidays to dress up for. Compared to the ugly Christmas sweater and a spooky Halloween costume, February 14th requires you to look your absolute best.

I know, the day before may entail some hair pulling and spontaneous online shopping—but we’re hoping that we made things a little easier for you. 

From slinky black dresses to adorable heart-printed sweaters, we’ve provided the creme-de-la-creme of Valentine’s Day outfits. Whether you’re dressing for your gal pals, your significant other, or for yourself, you deserve to look beautiful no matter what. 

Got any other fashion questions on your mind? Check out some of our articles:

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How To Wear Timberlands

How To Wear a Cowboy Hat

How To Wear Overalls

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