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)

Every item on this page was chosen by a The Pioneer Woman editor. We may earn commission on some of the items you choose to buy.

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

Bestseller

The Pioneer Woman Blanket Cardigan Sweater

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

3

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.

Advertisem*nt - Continue Reading Below

4

Bestseller

Chenille Yarn Valentine’s Day Sweatshirt

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

4

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.

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

Several Colors Available

Chenille Sweater Dress with Belt

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

6

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.

Advertisem*nt - Continue Reading Below

7

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 (9)

7

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.

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.

Advertisem*nt - Continue Reading Below

10

Ree's Style

The Pioneer Woman Keyhole Blouse

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

10

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!

11

For an Extra-Special Date

Alex Evenings Embroidered Dress

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

11

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.

12

Pretty in Pink

Heart Jacquard Bias Midi Skirt

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

12

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.

Advertisem*nt - Continue Reading Below

13

3,800+ Reviews

A-Line Swing Midi Dress

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

13

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!

14

Gorgeous Color

Red Sleeveless Wide-Leg Jumpsuit

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

14

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.

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."

Advertisem*nt - Continue Reading Below

16

Best Seller

Heart Relaxed Everyday Shirt

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

16

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.

17

Editor's Pick

Tory Heart Embroidered Pants

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

17

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.

18

Fun Find

Aliana Dress

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

18

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.

Advertisem*nt - Continue Reading Below

19

Casual Pick

Z Supply Coffee Sunday Sweatshirt

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

19

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.

20

13,000+ Reviews

Howdy Valentine Graphic Tee

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

20

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.

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 to wear on a Valentine's Day date? ›

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 the perfect date outfit? ›

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 a cute outfit to wear on a date? ›

If you want to really impress, wear a blazer with a button up shirt of you are in a more elegant setting. For women, go with a little black dress or a casual blouse and jeans finished with feminine accessories and a natural makeup look.

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 the dress code for Valentine's Day 2024? ›

What is the Valentine's Day dress code 2024? There is no fixed dress code for Valentine's Day. However, a lot of people wear red and pink outfits on this day as these colours are generally considered the colours of love and represent the spirit of love.

How do I choose a 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 color to wear on a date? ›

Wearing red might help you feel more attractive.

Red is always a powerful wardrobe choice and "obviously a great choice on a first date," Lewis said.

How do you look cute on a date? ›

For guys: Neat jeans (chinos are good), t-shirt or shirt and nice shoes. For a sunny day: For girls: A short, strapless, bright colored dress. Wear it with either matching gladiator sandals, or soft ballet flats, and a pretty necklace. If it's cold, cozy up with a sweatshirt.

How should I dress for a romantic night? ›

Seek for a snug fit: Go for date night outfits that are both comfortable and allow you to move around easily. You shouldn't be fiddling with your date dress the entire night. Choose a hue that complements your skin tone: When it comes to color, opt for a tint that matches your skin tone.

How do I look good on a date night? ›

You can't go wrong with a mini strapless dress and platform heels (we've also got some cute David Yurman jewelry alternatives to accessorize with, too!). If you're planning a Netflix and chill date night, opt for a more casual 'fit, like a pair of comfy sweatpants with an off-the-shoulder sweatshirt.

What to wear on your first night together? ›

Satin robes are a good option for nightwear for first wedding night. They simultaneously preserve your modesty while looking irresistible, so if you're a shy person, you can have the best of both worlds here! The robe can be a long one or a short one, based on your preference.

How do you look casual on a date? ›

Casual date outfit

Be yourself and be comfortable, but by all means, be put together, too. Avoid wrinkled clothes, too-snug shirts or jumpers, and too-short pants. Un-scuffed sneakers are fine, although loafers or boots might be better, depending on whether you're wearing jeans or khakis, respectively.

What are cute colors for Valentine's Day? ›

In the Valentine color palette, pink, purple, and red converge to create an enchanting symphony of love and romance.

What clothing is worn on Valentine's Day? ›

Stick With Traditional Colors

Red and pink make up the unofficial color palette of Valentine's Day for a reason, so if you're into a more traditional ensemble, Stein says let these romantic shades do the talking.

What colors represent Valentine's Day? ›

What are the Valentine's Day colors? 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.

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.

Should you go on a date on Valentines Day? ›

Valentine's Day isn't just for established couples. The day can set the scene for a fun first date, a therapist says. Dating experts suggest keeping things light with a drink or activity, like a game bar or arcade.

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

Create a homemade candlelit dinner

Plan a special menu together, light a few candles, and put on some romantic tunes that'll get sparks flying. You can even dress up and make it a fancy dinner, complete with table settings and your favourite wine.

Which colour is preferred on Valentine's Day? ›

Red: The undisputed champion

Red, the maestro of love's orchestra and an essential Valentine's Day color, takes center stage. Symbolizing passion and the fiery intensity of profound emotions, it's a classic choice that never fails to stir the heart.

References

Top Articles
Latest Posts
Article information

Author: Tish Haag

Last Updated:

Views: 5879

Rating: 4.7 / 5 (47 voted)

Reviews: 86% of readers found this page helpful

Author information

Name: Tish Haag

Birthday: 1999-11-18

Address: 30256 Tara Expressway, Kutchburgh, VT 92892-0078

Phone: +4215847628708

Job: Internal Consulting Engineer

Hobby: Roller skating, Roller skating, Kayaking, Flying, Graffiti, Ghost hunting, scrapbook

Introduction: My name is Tish Haag, I am a excited, delightful, curious, beautiful, agreeable, enchanting, fancy person who loves writing and wants to share my knowledge and understanding with you.