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 Blanket Cardigan Sweater

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

2

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.

3

Bestseller

Chenille Yarn Valentine’s Day Sweatshirt

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

3

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.

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4

Bestseller

The Pioneer Woman Flounce Sleeve Dress

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

4

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.

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.

6

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 (8)

6

Ree's Style

The Pioneer Woman Square Neck Blouse with Ruffle Sleeves

Now 23% 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.

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7

3,000+ Reviews

Chiffon Bell Sleeve Blouse

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

7

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!

8

Best Skirt

Express High Waisted Satin Side Slit Midi Skirt

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

8

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.

9

Comfiest Find

Burgundy Cable Knit Turtleneck Sweater Dress

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

9

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.

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10

3,800+ Reviews

A-Line Swing Midi Dress

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

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!

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

For an Extra-Special Date

Alex Evenings Embroidered Dress

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

12

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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13

Best Seller

Heart Relaxed Everyday Shirt

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

13

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.

14

Editor's Pick

Tory Heart Embroidered Pants

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

14

Editor's Pick

Tory Heart Embroidered Pants

Now 40% 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.

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

Casual Pick

Z Supply Coffee Sunday Sweatshirt

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

17

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.

18

13,000+ Reviews

Howdy Valentine Graphic Tee

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

18

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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19

Snuggly Sweater

Gap 24/7 Split-Hem Stripe Sweater

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

19

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!

20

Relaxed Vibes

Mauve Turtleneck Sweater Dress

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

20

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.

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 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 dress code for 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.

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.

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.

How to 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.

How can I look attractive on a date? ›

Both men and women are attracted to physical indications of health, such as shiny hair, clear skin, bright eyes, and a fit body. Try to have a symmetrical face. This can be hard to achieve at short notice, so it's a good idea to have your face sorted before you're asked out on a date. Having blue eyes also helps.

How should a girl dress on a date? ›

BEST FIRST DATE OUTFITS FOR WOMEN
  1. Crop Top And Jeans.
  2. Tank Top And Skirt.
  3. Jumpsuits.
  4. Floral Dress.
  5. Bodycon Dress.
  6. Off-shoulder Top And Pants.
  7. A T-Shirt and Jeans.
  8. Slip Skirt with Top.
Aug 18, 2023

What Colour is best to wear on a date? ›

Black is your go-to colour. A new study by Britain's University of Lincoln suggests that black beats red as the colour of choice when it comes to finding new love. The study explains how red increases the perceived sexual receptivity of the wearer, while black increases how fashionable the person is thought to be.

Can I wear purple on Valentine's Day? ›

Purple for Valentine's Day does not get enough credit. Lavender can be a very romantic color and is definitely in my top three for V-day. I recommend it as a subtle yet sassy statement. Lavender pairs extremely well with all the other colors on this list, so experiment!

What are Valentine's colors? ›

Valentine's Day celebrates love, affection, and romance, and its colors significantly convey the depth of these emotions. The traditional colors associated with Valentine's Day are red, white, and pink, each with symbolism and significance in love and relationships.

What does purple mean on Valentine's Day? ›

With ties to nobility and royalty, purple roses tell the one you love that she is the most important woman in your life, and your queen.

What should date night look like? ›

A date night is an occasion where a couple dedicates time to be spent together, usually alone, with the purpose of reconnecting and bonding. A date night usually consists of a main activity, such as a dinner and/or a movie, or a few activities planned one after the other.

What should a 50 year old woman wear on a date? ›

A silk blouse or a V-neck sweater with low heels or pointy flats looks feminine and polished; a simple white T-shirt or crisp white shirt with sleeves turned up and rolled with leather ankle boots looks classy and classic. White jeans with a black blouse or sweater and your black belt are always memorable.

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.

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

Red means love, symbolic of the heart, and the red rose was the favorite flower of Venus, the Roman goddess of love. Red and white, make pink. Red is usually reserved for romantic, intimate relationships and pink can be for close friends or family members on Valentine's Day.

Can I wear jeans on Valentine's Day? ›

I'd take a subtle yet festive approach and wear excellent-fitting jeans, a top with a pop of red or pink, and some fun accessories and dainty lingerie (for your own confidence boost, natch). This formula works for dinner in a chic restaurant, an at-home meal, or something off-piste like… bowling.

How do I prepare for a Valentine's date? ›

Plan a special outing.

Try for an activity that you don't get to do together often, or that your date has been wanting to do for awhile. Check event locations for special Valentine's Day parties, activities, or discounts to take advantage of. Choose activities perfect for two to create an intimate date.

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