Casual Valentine’s Day Outfit Ideas for Every Kind of Date (2024)

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More than anything, Valentine’s Day is an opportunity for all of us to take a second and appreciate the love around us – whether it be with a significant other, dear friends, or even our family!

However you plan on celebrating the occasion this year, there are tons of different ways to implement a festive touch or two to your casual outfit – after all, who doesn’t love adding a little something special when the date calls for celebration?

From taking a romantic afternoon day date to enjoying a special at-homedinner or a casual movie night, we have curated a list of outfits that have got you covered all throughout the most romantic day of the year, no matter what your weather – or plans – look like! Let’s get into it.

1. striped sweater + straight jeans + platform loafers + shoulder bag

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (1)

sweater | jeans | shoes | bag

If you’re looking for a simple yet fun way to add a little V-day spice to an everyday look, this outfit is the way to do it.

Integrating the trademark Valentine’s Day colors into our outfits for the day might be simple in theory, but it doesn’t always come naturally to those of us who tend to lean more towards more muted, neutral tones in our wardrobe.

Adding a dash of color through this striped sweater allows us to let the festive energy in without having to compromise our sense of personal style – and keep a sweater we know we’ll be able to wear and love for years to come! Beyond its use of color, this sweater features an oversized fit that gives your overall look a cool, laid-back feel without being too relaxed.

On the bottom, these high-waisted jeans keep things beyond flattering, betting on a well-loved design with clean features. The straight fit of this pair of jeans balances out the oversized fit of the sweater, making for the perfect combination.

For shoes, there’s no going wrong with a classic pair of black loafers for both a modern and timeless touch at the same time (who doesn’t love the cyclical nature of fashion?!) Finish off this outfit with this small shoulder bag that can be worn both crossbody and over your shoulder to complement whatever mood you’re going for.

2. knit sweater + wide-leg corduroy pants + mules + leather tote + earrings

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (2)

sweater | pants | shoes | bag | earrings

Monochromatic looks might not be the first thing that comes to mind when we think about Valentine’s Day outfits, but it definitely catches the eye. Classy Valentine’s Day outfits can go far beyond fancy dresses and black heels!

For this look we’re going in a more subtly romantic, chic direction, starting with this knit sweater. The delicate detail work of this knit embodies femininity in its own subtle way, making it the perfect contender for your Valentine’s Day plans.

On the bottom, this pair of white, wide-leg corduroy pants are the perfect match, bringing in their fair share of texture, extra warmth, and structure to the overall look. For extra styling points, try tucking in your cozy sweaters slightly at the front!

Your accessories work to tie your outfit together, bringing in slightly darker neutral shades for elegant accents that still maintain the subtlety of the original proposal.

This heeled, pointed-toe mule does just that, adding a touch of sophistication through its refined design and neutral shade. For the final touches, this small leather tote adds structure and an added chic touch, while the intertwined gold earrings contribute some more feminine flair. Want an even more special nod to the date? Add your favorite red lip to your ensemble!

3. ruffled openwork vest + jean + Mary Jane flat + shoulder bag

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (3)

vest | jeans | shoes | bag

Sweater vests are high-ticket items in the current world of fashion, and it’s not hard to get why. Versatile, fun, and chic, varieties of this style rank high on many of our current wish lists.

Beyond its appealing aesthetic, sweater vests are also great transition pieces to include in our closets as we inch closer to spring. While they are great to be worn layered with other pieces during the colder months of the year, they can also be worn by themselves to produce a refined, sophisticated outfit.

We know – Valentine’s Day doesn’t quite mean spring has arrived, but sweater vests are still perfect for those who find themselves in warmer states this coming month. This piece allows you to still adhere to the appropriate season, while at the same time staying comfortable and more chic than ever.

This ruffle openwork vest is the perfect contender for the occasion, sprinkling in a gorgeous, slightly muted pink color and feminine details for the ideal Valentine’s Day celebration look.

If hot pink isn’t your thing, there’s no reason to have to commit to only bold colors to make your outfit work for your romantic look. Beyond adding just the perfect shade to the ensemble, this sweater vest combo is also extremely versatile for whatever you have planned throughout your favorite hallmark holiday.

Pair your gorgeous sweater vest with these high-waisted jeans that feature a more-than-flattering fit and give you an elongated silhouette. We love the subtle touches around here, and the two-toned hem detailing on this design gives it yet another layer of its own special flair. For shoes, these square-toe Mary Jane flats bring in a touch of the current trends while still keeping this outfit classic. Finish it off with this brown shoulder bag for the ultimate cherry on top.

4. sweater tank + maxi skirt + Adidas Sambas sneakers + shoulder bag

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (4)

top | skirt | sneakers | bag

If you’re going for modern and ultra-chic, four might be your lucky number. This look bets on well-fitted pieces and a very popular trending item to pull it together – if you care about trends, that is!

For this particular look, let’s get things started with this twill maxi skirt. Its tailored design immediately sets the tone with its chic, elevated feel. To build on this, pair this skirt with this rib mock neck sweater tank.

Pairing seamlessly with the skirt, this sweater tank works to create a smooth, long line in your look, as well as elongating your torso with its high neckline and fitted design.

The Adidas Sambas have won over the hearts of many throughout this last year, and we have to agree with the hype. As an extremely versatile shoe, this design gives us plenty of options when it comes to styling – both with a more casual look and with elevated versions of everyday outfits.

Pair your Sambas with this look, adding a touch of casual without compromising the elegant feel of the outfit. For balance and a perfect final touch, add this small shoulder bag with its matching sleek, modern shape.

5. turtleneck sweater + jeans + loafer

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (5)

sweater | jeans | shoes

This next look focuses on keeping you warm and comfortable, while also making sure to sneak in a special element the occasion calls for.

This wide rib turtleneck sweater is a winter closet staple, and there’s nothing better than using it to snuggle up on a chilly February evening – whether it be in a movie theater or a cozy Italian eatery.

For pants, these jeans feature the most flattering fit, ensuring a super high waist and a design that hugs your figure in all of the right places. On the bottom, trade in your go-to black feels and finish off this simple, cozy look with a pair of festive red loafers for a stunning and unconventional pop of color.

After all, a romantic evening is the perfect excuse to try something different while still keeping things laid back!

6. rib-knit dress + mules + drop earrings

dress | mule | earrings

For those who find themselves in warmer climates for the day of love, there’s nothing quite like finding a great dress for a gorgeous, quick, and easy outfit that will make you look like you spent a lot more time getting ready than you did.

This rib-knit, midi dress features a simple, clean design that makes for a sleek end result. While this dress would also be great for statement accessories, we’ve decided to let the color shine in honor of V-Day, making it the main event for this look.

Pair this dress with a pair of small gold hoop earrings for an added touch of delicate femininity, and finish off with these nude mules with a front bow detail that pays an ode to one of this year’s newest and hottest styles!

7. wool blazer + cotton tee + slim wide-leg jean + ballet flat

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (7)

blazer | tee | jeans | shoes

For more casual looks, there’s no need to only stick to the obvious. While we love sweaters, for example, there’s nothing wrong with wanting to dress up a little more while still keeping the feel of your outfit more laid-back.

This red blazer is the perfect piece to help you achieve just that – a date-appropriate, fun, way to add color to your look while also making for a balanced and gorgeous outfit we bet you’ll keep coming back to way after V-day’s over.

For this look, starting with a strong foundation is half the battle! A great pair of blue jeans and a well-fitting white tee can do wonders when it comes to setting the tone for this outfit; after all, a good fit in clothes makes or breaks any look regardless of how amazing the designs might be on their own.

This white cotton t-shirt and slim wide-leg jeans create a great base of timeless staples. On top, layer this sculpted Italian wool blazer for a touch of warmth and, of course, great style.

Add a touch of current yet classic charm with this pair of nude ballet flats to give your outfit the final touch it needs.

8. shift dress + flat + handbag

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (8)

dress | flat | bag

If a fancy, romantic dinner reservation is on the horizon for your Valentine’s Day, then a charming and elegant dress is a great choice for your celebration while still keeping things casual.

This black outfit steers away from the colorful versions of the other looks, playing instead a different angle more geared towards a classic date outfit that you’ll get lots of wear out of for plenty of occasions beyond V-Day.

Start your look off with this button-front shift dress, made from a drapey crepe fabric that lends a flowy feel to the piece. In contrast with its fabric, its more structured design brings true balance to the final result, making this dress both comfortable and elevated at once.

While we love small clutches and crossbody bags, this mid-sized shoulder bag pairs beautifully with this look, bringing in texture without steering away from the aesthetic of this little black dress. Its slouchy silhouette also makes this accessory the more interesting choice, providing plenty of room for all of your date essentials and making for a larger element that brings balance to this sleek look.

For shoes, there’s no going wrong with a classic pair of ballet flats. Versatile, comfortable, and always chic, this shoe will guarantee a perfect finishing touch to your ensemble while slightly dressing down your look and making it perfect wherever you go!

9. polo neck sweater + wide-leg jeans + slingback pump + heart earrings

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (9)

sweater | jeans | shoes | earrings

If you’re anticipating a busy Valentine’s Day ahead, transitional looks that can easily go from day to night are the perfect contenders for you.

This look in particular leans on the more casual side, still bringing plenty of class and personality for a well-rounded and festive look that won’t let the day go by unnoticed.

Start with these super wide-leg jeans for your base. With seam details that go up the legs, these trousers give off the look of classic denim while also adding a little extra something for added flair. Beyond contributing an aesthetic factor, these seams also work to elongate your figure as a whole!

On top, this knitted polo neck sweater is the perfect choice to blend day and night, keeping things neutral with its color palette while still appropriate for your Valentine’s Day dinner or drinks.

These pointed-toe slingback pumps provide an elegant edge of their own with an outer suede lining, while also keeping you comfortable and secure through an elasticized slingback strap.

Bring in a fun and funky special touch for the occasion with these beaded fringe heart earrings – the perfect option for bringing both a pop of color and an accessory to balance out the elegant and timeless feel of the look. If taking this outfit directly from the office to your date, we recommend you put your hair up and throw on a swipe of red lipstick for some more V-day charm!

10. ribbed midi skirt + turtleneck + knee-high boot + flower stud earrings

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (10)

skirt | turtleneck | boots | earrings

This sophisticated outfit once again steers away from integrating the trademark colors of the holiday of love in the more obvious ways, while still finding a way to add a touch of the occasion to the final look.

Made from fine kit fabric, this ribbed midi skirt features movement and an elasticated waist that makes this design easy to wear. Elegant in both its cut and color, this skirt is sure to make the rounds in your closet for a variety of different outfits.

On top, a classic turtleneck pairs perfectly with the bottom part of the look, resulting in a warm and cohesive outfit that screams “chic!”

Coordinate your knee-high boots with your top, bringing in just the right amount of these deep earth tones to balance the neutral shade of the skirt. For your main accessory, these beaded flower stud earrings allow you to bring in a subtle and elegant pop of red to celebrate this special date.

11. knit shirt + ribbed midi skirt + double strap Mary Janes + small hoop earrings

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (11)

top | skirt | shoes | earrings

Delicate and feminine looks don’t have to be limited to light neutrals or colorful pops of color to work for your special date this February.

Integrating the bow trend in a subtle and understated way, this top and skirt set is the perfect way to dress romantic and appropriate while still maintaining your own personal aesthetic.

To soften the look every so slightly, these double-strap Mary Jane flats add an extra touch of delicate femininity while still keeping things contemporary and ever-so-chic.

To top it all off, add a small but charming pair of small hoop earrings to your ensemble.

Finding Your Perfect Casual Valentine’s Day Outfit Ideas

From subtle nods to traditional Valentine’s Day colors to unique, understated details, each of these outfits tells a story of individual style and celebrates the joy of expressing ourselves through fashion that makes us feel good. There are no wrong answers!

So, whether you find yourself in a cozy sweater on a chilly evening or a sophisticated dress for a fancy dinner, remember that the most important element of any outfit is the confidence and joy it brings. Here’s to a Valentine’s Day filled with love, laughter, and the perfect outfit that makes you feel truly special – and cheers to love!

Does your weather lean more cold and windy than warm and sunny? If you live in a cold climate, we have Valentine’s Day outfit ideas specifically for you: Cute Valentine’s Day Outfits for Your Winter Dates

Casual Valentine’s Day Outfit Ideas for Every Kind of Date (2024)


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