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

Now 43% Off

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

The Pioneer Woman Flounce Sleeve Dress

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

2

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.

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

3,000+ Reviews

Chiffon Bell Sleeve Blouse

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

4

3,000+ Reviews

Chiffon Bell Sleeve Blouse

Now 30% Off

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!

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.

6

Best Seller

Heart Relaxed Everyday Shirt

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

6

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.

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7

3,800+ Reviews

A-Line Swing Midi Dress

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

7

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!

8

Bestseller

Chenille Yarn Valentine’s Day Sweatshirt

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

8

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.

9

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 (11)

9

Ree's Style

The Pioneer Woman Square Neck Blouse with Ruffle Sleeves

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.

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10

For an Extra-Special Date

Alex Evenings Embroidered Dress

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

10

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.

11

Pretty in Pink

Heart Jacquard Bias Midi Skirt

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

11

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.

12

13,000+ Reviews

Howdy Valentine Graphic Tee

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

12

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.

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13

Best Skirt

Express High Waisted Satin Side Slit Midi Skirt

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

13

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.

14

Comfiest Find

Burgundy Cable Knit Turtleneck Sweater Dress

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

14

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.

15

Best Pants

Ribcage Straight Ankle Corduroy Pants

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

15

Best Pants

Ribcage Straight Ankle Corduroy Pants

Now 44% Off

Pair these corduroy pants with a simple tee or sweater to set the mood. You'll enjoy the fan favorite high fitted waist and slouchy straight leg fit. The color is so fitting for the holiday: "Decadent Chocolate Red."

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16

Ree's Style

The Pioneer Woman Keyhole Blouse

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

16

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!

17

Just Fancy Enough

Mock Neck Tiered Mini Dress

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

17

Just Fancy Enough

Mock Neck Tiered Mini Dress

Now 44% Off

There's something so special about the ruched fabric of this tiered mini dress. Statement sleeves and ruffle details add to the fun.

18

5-Star Rating

The Pioneer Woman Tiered Ruffle Dress with Long Sleeves

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

18

5-Star Rating

The Pioneer Woman Tiered Ruffle Dress with Long Sleeves

You can't go wrong with any of the floral dresses from Ree's winter apparel collection at Walmart, but this one in a color called "Electric Floral Tibetan Red" is particularly on point.

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19

Fun Find

Aliana Dress

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

19

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.

20

Casual Pick

Z Supply Coffee Sunday Sweatshirt

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

20

Casual Pick

Z Supply Coffee Sunday Sweatshirt

Breakfast in bed, anyone? Give your sweetheart a little hint when you pull on this oversized sweatshirt that reads "bring me coffee in bed." Considering it has soft brushed fleece, you probably won't want to take it off.

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

Macie Reynolds

Assistant Editor

Macie Reynolds is the assistant editor of E-Commerce and SEO for The Pioneer Woman.

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

FAQs

What is a good outfit for Valentine's Day? ›

A cute casual dress or co*cktail dress is the perfect compromise between the ultra-sexy, romantic Valentine's Day getup and your favorite daytime look. Colors like dark burgundy or pure white are perfect for a simple, sweet vibe, but patterns can also bring a bit of sophistication into the mix.

What is your ideal romantic Valentine's night? ›

Arrange a Romantic Dinner

Take the average dinner date up a notch for Valentine's Day by reserving a private dining experience. Or, enjoy a cozy candlelit dinner at home catered by your favorite restaurant. Make it a truly special meal together with flowers and decorations, and set the mood with some romantic music.

What clothing is worn on Valentine's Day? ›

Pink and Red are the most commonly worn colours on Valentine's Day. These also happen to be one of the best colour combinations for a statement outfit. Red signifies love and pink means gentleness. However, if you like both colours, you can opt for them both.

How do you make a girl feel special on Valentine's Day? ›

Never mind, there are ways you can adopt to make sure she doesn't miss out on this special day.
  1. Plan a date. ...
  2. Shop for her. ...
  3. Buy her a pet. ...
  4. Go adventurous. ...
  5. Learn a skill together. ...
  6. Go to a concert. ...
  7. Revisit the first date. ...
  8. Write a letter.
Jan 22, 2024

What is a cute Valentine's Day tradition? ›

Offering a bouquet of red roses to your beloved. Purchasing a card with a heartfelt message. Sharing a candlelit meal with your partner. Giving a heart-shaped box of delicious chocolates.

What is the dress code for Valentine dinner? ›

Casual Elegant

This will vary, depending on the extent you want to dress up. For him, wear a dark suit or a button down with trousers, and a sports coat. For her, a formal pants outfit, or a chic black dress with an evening wrap or an envelope clutch bag. Use your finer jewelry, bold makeup, and show some skin.

What does wearing pink on Valentine's Day mean? ›

Pink is often seen as a softer and more youthful version of red and stands for young love, femininity, innocence, and purity. In addition, many of the favorite flowers for Valentine's Day, such as roses, carnations, and tulips, come in both shades, which makes the connection even stronger.

What does it mean if you wear white on Valentine's Day? ›

WHITE. You often also see a lot of white on Valentine's Day, and when you look into white as being a part of the dress code it connects to being “reserved” or the fact that you have accepted a proposal and you're on your way to being married.

What does wearing red on Valentine's Day mean? ›

Firstly, red is associated with the heart, which is the centre of love and emotion. The heart is often depicted as a bright red symbol, and this association has helped make red a powerful symbol of love. Another reason why red is the colour of love is because of its association with desire and passion.

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

Cute Valentine's Day Quotes
  • “You are the person I never knew how to write, and this life is the story I have always wanted to tell.” — ...
  • “Unless you love someone, nothing else makes sense.” — ...
  • “You are what I never knew I always wanted.” — ...
  • “For love, I'd do anything.
Jan 5, 2024

How do you have the perfect Valentine's Day? ›

Prepare a Special Meal

If you or your partner like to cook, go all out with a multi-course Valentine's Day dinner. Or put a twist on it—maybe you want to make it a night of quick appetizers or serve a slew of aphrodisiacs in your feast. Or, instead of a full dinner, indulge in a dessert-only menu for your at-home date.

How do I make my Valentine special? ›

Spending Quality Time Together

Often just putting something together in advance is a good way to show your valentine that you care and that you're thinking of them. Add some candles, turn down the lights, and it's a perfect romantic evening. Plan a day out.

Which colour dress is best for Valentine's Day? ›

Traditionally red is the best colour for your Valentine's Day outfit symbolising love and passion. Opt for a bold raspberry hue, a playful cherry red, or a sophisticated burgundy for a modern twist.

What is a nice color for Valentine's Day? ›

30 best Valentine's Day color schemes with the red of love, pink for gentleness, gold for trust, lavender for passion, burgundy for care and much more.

What is the love color for 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.

What color are hearts for Valentine's Day? ›

Red is the color of the heart and blood, and that is why it is connected to love and passion. Since it is linked to the heart and blood, it is connected to romantic love.

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