These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (2024)

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (1)

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Don't get us wrong: Comfy, warm leggings are downright fabulous (and Ree Drummond appreciates them, too!). But when February 14 rolls around, it can be nice to dress up a little—particularly if you've been sporting those leggings every other day of the week. So, if you're wanting to show off your style this year, and get a little festive while you're at it, try one of these Valentine's Day outfits. And be sure to pair them with some fun Valentine's Day earrings and Valentine's Day nail designs, too!

Here, we've curated a list of the cutest, most on-theme Valentine's Day outfits for both an at-home dinner for two or out-on-the-town date nights. You could even wear one for your Galentine's Day party. They're lovely, sophisticated, and still every bit as comfy as your favorite yoga pants—in fact, we've even got an elevated pair of Valentine's Day pajamas on our list. (Who says you can't dress up just because you plan to spend the evening watching romantic movies at home?)

Cute oversized sweaters abound here, as do flowy Valentine's Day dresses, statement pants, festive graphic tees, winter skirts, and head-turning jumpsuits. And of course, you'll find plenty of options here from Ree's winter clothing line at Walmart, including a pink cardigan sweater with the dreamiest pointelle stitch design and of course, blouses galore featuring her signature floral prints. Pair them with your best jeans, add a pair of cowgirl boots or, well, any cute pair of boots, and prepare to make your date swoon.

1

Best Sweater

Heart Print Sweater

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (3)

1

Best Sweater

Heart Print Sweater

Here's one way to wear your heart on your sleeve! This sweater with its soft knit and playful pattern will keep you perfectly on-trend and just as cozy.

2

Bestseller

Chenille Yarn Valentine’s Day Sweatshirt

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (4)

2

Bestseller

Chenille Yarn Valentine’s Day Sweatshirt

Whether you wear it out and about or while cozied up at home, the "XOXO" embroidery on this sweatshirt brings so much festive fun! You can get the sweatshirt in so many different colors, too.

3

Several Colors Available

Chenille Sweater Dress with Belt

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (5)

3

Several Colors Available

Chenille Sweater Dress with Belt

Now 46% Off

Dressed-up date night, here you come! This hot pink sweater dress complete with soft chenille yarn, lantern sleeves, and a belt (!) is perfectly on-theme.

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4

Ree's Style

The Pioneer Woman Square Neck Blouse with Ruffle Sleeves

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (6)

4

Ree's Style

The Pioneer Woman Square Neck Blouse with Ruffle Sleeves

Now 18% Off

The bright pink color of this darling dotted blouse screams February 14, but thanks to that blousy design complete with ruffle sleeves, you'll want to wear it for the rest of the season, too.

With the right pants, this versatile blouse can easily take you from work to date night. The chiffon fabric, keyhole back, and ruffle detail on the sleeves makes it oh-so-chic!

6

Bestseller

The Pioneer Woman Flounce Sleeve Dress

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (8)

6

Bestseller

The Pioneer Woman Flounce Sleeve Dress

Add instant femininity to your look with this lightweight dress from Ree's Walmart collection. The sweet eyelet trim and tiered skirt keep it relaxed but elevated, and will help you create the perfect atmosphere for any date.

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7

Best Skirt

Express High Waisted Satin Side Slit Midi Skirt

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (9)

7

Best Skirt

Express High Waisted Satin Side Slit Midi Skirt

You can never go wrong with a satin fabrication for a fancy outing! This midi skirt option has a bold red color and a side slit for extra oomph.

8

3,800+ Reviews

A-Line Swing Midi Dress

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (10)

8

3,800+ Reviews

A-Line Swing Midi Dress

Talk about an easy-to-wear outfit: The knit jersey that makes up this dress is incredibly soft and breezy, so it drapes beautifully. It comes in plus sizes, too!

9

Ree's Style

The Pioneer Woman Keyhole Blouse

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (11)

9

Ree's Style

The Pioneer Woman Keyhole Blouse

How cute is this jacquard rose print number from Ree's collection? It couldn't be more fabulous and festive!

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10

Relaxed Vibes

Mauve Turtleneck Sweater Dress

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (12)

10

Relaxed Vibes

Mauve Turtleneck Sweater Dress

Soft and, yes, stretchy, this pink turtleneck dress is just begging to be worn on Valentine's Day. You'll feel equal parts comfy and cool.

11

Gorgeous Color

Red Sleeveless Wide-Leg Jumpsuit

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (13)

11

Gorgeous Color

Red Sleeveless Wide-Leg Jumpsuit

Looking to turn heads? This stretch-knit jumpsuit pairs a plunging neckline with sophisticated-looking wide-leg pants for the ultimate statement.

12

Fun Find

Aliana Dress

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (14)

12

Fun Find

Aliana Dress

We wouldn't be surprised if this pink and red color block dress came straight from Cupid himself. It's super fun for a date night and can be paired with a cardigan for extra warmth.

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13

Editor's Pick

Tory Heart Embroidered Pants

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (15)

13

Editor's Pick

Tory Heart Embroidered Pants

Now 30% Off

You don't have to stick with tried-and-true pinks and reds on Valentine's Day! Black and white can be equally alluring, especially when designed with a festive pattern.

14

13,000+ Reviews

Howdy Valentine Graphic Tee

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (16)

14

13,000+ Reviews

Howdy Valentine Graphic Tee

Time to sweeten up your style—in a cowgirl chic way, of course. This graphic tee boasts an adorable cupid riding a horse with the text "Howdy Valentine" for a little western flair that you can't pass up.

15

Snuggly Sweater

Gap 24/7 Split-Hem Stripe Sweater

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (17)

15

Snuggly Sweater

Gap 24/7 Split-Hem Stripe Sweater

Dreamy shades of pink come together in this charming striped knit. You'll want to pull it out again as soon as that next snowstorm hits, too!

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16

Pretty in Pink

Heart Jacquard Bias Midi Skirt

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (18)

16

Pretty in Pink

Heart Jacquard Bias Midi Skirt

Now 40% Off

How sweet are the mini heart motifs that fill this midi skirt? Add a favorite tee or a comfy sweater to complete the look.

17

Comfiest Find

Burgundy Cable Knit Turtleneck Sweater Dress

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (19)

17

Comfiest Find

Burgundy Cable Knit Turtleneck Sweater Dress

Prepare to get cozy! This knit dress is a delight to wear, featuring warm fabric, a flirty length, and an oversized silhouette.

18

For an Extra-Special Date

Alex Evenings Embroidered Dress

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (20)

18

For an Extra-Special Date

Alex Evenings Embroidered Dress

An all-over embroidered pattern dotted with shiny sequins makes this dress a guaranteed winner. We love the cap sleeves and just-below-the-knee flared length.

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19

Bestseller

The Pioneer Woman Blanket Cardigan Sweater

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (21)

19

Bestseller

The Pioneer Woman Blanket Cardigan Sweater

Now 37% Off

The dreamiest jacquard floral pattern in a pointelle stitch awaits you thanks to this cardigan from Ree's line. Throw it on over any blouse or dress! And if that "Sweet Rose" color isn't perfectly right for the occasion, we don't know what is.

20

Best Seller

Heart Relaxed Everyday Shirt

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (22)

20

Best Seller

Heart Relaxed Everyday Shirt

Now 40% Off

There's no better way to show your love on Valentine's Day than to have it displayed on your shirt. This button-down can be worn casually with jeans or dressed up with a skirt.

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (23)

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Valentine's Day Outfits

Valentine's Day is a great opportunity to dress up and showcase your style. Whether it's for an at-home dinner, a night out, or a Galentine's Day party, there are plenty of outfit options to consider. From cute oversized sweaters to flowy dresses, statement pants, and head-turning jumpsuits, there's something for everyone's taste and preference.

Valentine's Day Outfit Ideas:

  • Heart Print Sweater: A soft knit sweater with a playful pattern to keep you on-trend and cozy.
  • Chenille Yarn Valentine’s Day Sweatshirt: Featuring "XOXO" embroidery for festive fun.
  • Chenille Sweater Dress with Belt: A hot pink sweater dress with lantern sleeves and a belt for a dressed-up date night look.
  • The Pioneer Woman Square Neck Blouse with Ruffle Sleeves: A bright pink blouse with a blousy design and ruffle sleeves, perfect for the season.
  • Chiffon Bell Sleeve Blouse: A versatile blouse with chiffon fabric, keyhole back, and ruffle detail on the sleeves.
  • The Pioneer Woman Flounce Sleeve Dress: A lightweight dress with eyelet trim and a tiered skirt for a relaxed yet elevated look.
  • Express High Waisted Satin Side Slit Midi Skirt: A bold red satin midi skirt for a fancy outing.
  • A-Line Swing Midi Dress: An easy-to-wear outfit with soft and breezy knit jersey, available in plus sizes.
  • The Pioneer Woman Keyhole Blouse: A jacquard rose print blouse for a fabulous and festive look.
  • Mauve Turtleneck Sweater Dress: A soft and stretchy pink turtleneck dress for a comfortable yet stylish option.
  • Red Sleeveless Wide-Leg Jumpsuit: A stretch-knit jumpsuit with a plunging neckline and wide-leg pants for a head-turning statement.
  • Aliana Dress: A pink and red color block dress for a fun and stylish date night look.
  • Tory Heart Embroidered Pants: Black and white pants with a festive heart pattern for a unique Valentine's Day outfit.
  • Howdy Valentine Graphic Tee: A graphic tee with a western flair featuring an adorable cupid riding a horse.
  • Gap 24/7 Split-Hem Stripe Sweater: A charming striped knit sweater in dreamy shades of pink.
  • Heart Jacquard Bias Midi Skirt: A midi skirt with mini heart motifs for a sweet and stylish look.
  • Burgundy Cable Knit Turtleneck Sweater Dress: A cozy knit dress with warm fabric and an oversized silhouette.
  • Alex Evenings Embroidered Dress: An all-over embroidered dress with shiny sequins for an extra-special date.
  • The Pioneer Woman Blanket Cardigan Sweater: A jacquard floral pattern cardigan in a pointelle stitch for a dreamy look.
  • Heart Relaxed Everyday Shirt: A button-down shirt with a heart design for a casual yet festive look.

These outfit ideas cater to various styles and preferences, ensuring that everyone can find the perfect Valentine's Day ensemble.

I hope you find these outfit ideas helpful for celebrating Valentine's Day in style!

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (2024)

FAQs

What should I wear on Valentines Day date? ›

If you're looking for cute Valentine's Day outfit ideas that ooze sweet + romantic vibes, you can never go wrong with Cupid's favorite color palette. We're talking bold reds, pretty pinks, and soft shades of white, cream, and blush. If it makes you feel like a walking valentine, you're on the right track!

What is the perfect date outfit? ›

You want your outfit to feel as laid-back as the date. "Opt for a casual, easy vibe," Priyanka says. "Keeping it low-key is the main focus." As jeans are practically the definition of casual, they're an ideal choice. "Light-wash, high-waist denim with a T-shirt is a great look and also very classic," Priyanka notes.

What is the best clothing for Valentine's Day? ›

If you want to wear red or pink, the traditional colors of love, you can choose a dress, a skirt, a top, or even a pair of pants in these hues. You can also mix and match them with other colors, such as black, white, or beige, for a more balanced look. How do I choose the best Valentine's Day dress code?

How can I look cute on Valentine's Day? ›

Try a classically romantic outfit.

When shopping for your Valentine's Day outfit, search for romantic elements and details, such as puffed sleeves, lace, or ribbon details. For a romantic look that is always in style, try wearing clean and simple winter whites for your Valentine's Day outing.

Can I wear black on Valentine's Day? ›

If wear all black, together we can make a statement. A statement that we don't need one day a year to show love to others. We shouldn't need an excuse to show love. Whether that being love to another individual or to yourself.

What's the most popular shape on Valentine's Day? ›

Be it a cake, a balloon, or any gift, the heart shape dominates the shelves of all stores for Valentine's Day gifts. Love has always been associated with the heart since ancient times, and the same goes for feelings and emotions. A red heart pierced by Cupid's arrow is a conventional love symbol.

What is the best color to wear on a date? ›

When in Doubt, Wear Red or Black. According to color psychologists, the best colors to wear on a first date are red & black. Wearing the two romantic colors, especially if you're a woman, can make you appear more attractive and more desirable to your date.

What do girls wear on dates? ›

For a casual coffee date, opt for well-fitted jeans or a stylish skirt paired with a flattering crop top or casual, chic blouse. Complete the look with comfortable flats or ankle boots, minimal accessories, and light, natural makeup.

What is date night dress code? ›

Cute and casual date night outfits can be as basic as jeans and a graphic t-shirt to dresses and flirty sandals for the ladies. For men, jeans are most common and are easy to elevate with a crisp button-down shirt or a sport coat over a tee.

What is the most popular color on Valentine's Day? ›

Reds and pinks pair well with white and pastel colors, too. In general, pink is the definitive color of Valentine's Day. (Plus, it's my girlfriend's favorite.)

What color suit for Valentine's Day? ›

1. What men should wear to Valentine's Day dinner date? Grey, blue, or black suits are usually a good choice as Valentine's day outfits for guys. For outerwear, don an overcoat or a peacoat for a complete traditional appearance.

Which colour is best on Valentine's Day? ›

Red, the quintessential colour of love, symbolizes passion, desire, and romance. When used in Valentine's Day decor, it evokes feelings of warmth and intensity.

Do you dress up on Valentine's Day? ›

Whether it's a party for singles, a special Valentine's event or just for a bit of fun with your other half, dressing up is a brilliant way to get you in the mood for love.

What is Secret Valentine's? ›

Celebrate Galentine's Day with a Valentine's Secret Santa for the true loves in your life: your besties! Draw names online and find the perfect gift for your Secret Cupid. Who will be your Valentine's Secret Santa? Start a Secret Valentine gift exchange, spread the love and find out.

What color should I wear on Valentines date? ›

Red: In Love

First on the list is the colour Red, which stands for love and romance. To let others know you are already in love, dress up in a red outfit and go on a candlelight date with your loved one. Make the day extra special by choosing Valentine's gifts for her, like chocolates, flowers and plushies.

What color do you wear on Valentines Day if you are single? ›

GREY. Within the Valentine's Day dress code, grey means that you're just not interested in pursuing any type of relationship. You're at a good state with yourself and you don't have any other colors to wear to symbolize any type of relationship status or the readiness for another one.

What color can you wear for Valentine's Day? ›

Pop into any flower shop or even a festive hotel or restaurant and there's no arguing that red, white, and pink are the official colors of Valentine's Day. As a holiday centered around love and romance, it's no surprise that these bold colors with their rich pasts are associated with the celebration.

Should I wear red or white on Valentine's Day? ›

Saint Valentine was a patron and Christian martyr that historians believe was present around A.D. 270. It is because of him that we celebrate Valentine's Day today, and wear red likely because it was the color of choice for cardinals and popes.

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