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)

Macie Reynolds

Assistant Editor

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

Insights, advice, suggestions, feedback and comments from experts

I am an expert and enthusiast-based assistant. I have access to a wide range of information and can provide assistance on various topics. I can help answer questions, provide information, and engage in discussions. If you have any questions or need assistance, feel free to ask!

Now, let's discuss the concepts mentioned in this article.

Valentine's Day Outfits:

The article discusses various Valentine's Day outfits that can be worn for different occasions, such as an at-home dinner, a date night, or a Galentine's Day party. The outfits range from cute oversized sweaters, flowy dresses, statement pants, winter skirts, jumpsuits, and more. The article also mentions the availability of Valentine's Day-themed clothing from Ree Drummond's winter clothing line at Walmart, including a pink cardigan sweater and blouses with floral prints.

Valentine's Day Earrings and Nail Designs:

In addition to outfits, the article suggests pairing the Valentine's Day outfits with fun Valentine's Day earrings and nail designs. These accessories can add a festive touch to the overall look and help showcase personal style.

It's important to note that the information provided above is based on this article. If you have any specific questions or need further information, feel free to ask!

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

FAQs

What should I 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? ›

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 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.

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.

What is the best color to wear on 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.

What to wear on Valentine's Day for females? ›

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. “Try combining the colors, perhaps a red tulle midi skirt and a fuchsia sweater with coordinating fuchsia pumps,” she recommends.

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.

How to dress for a date female? ›

5 Simple Tips on How to Dress for a First Date for Women
  1. Dress comfortably. You will exude confidence and appear relaxed if you dress in a comfortable outfit. ...
  2. Dress for the occasion. ...
  3. Be yourself. ...
  4. Go for black and red outfits. ...
  5. Follow the third piece rule.
Apr 26, 2023

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.

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 do girls wear on first night? ›

Consider a special lingerie set, such as a lace or a satin babydoll, to create a romantic and intimate atmosphere on your honeymoon's first night. Choose something that makes you feel confident and beautiful.

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.

What to wear on Feb 14th? ›

The colours associated with Valentine's Day are Red, Yellow, Orange, Blue, Pink, Black, Green, White, Grey and Brown. Each of these colours denotes a different kind of love. Pink and Red are the most commonly worn colours on Valentine's Day.

How can I look cute and sweet? ›

If you're trying to look cute, wear cute clothes, like skirts or dresses instead of pants or shorts. Also, choose clothes in pastel colors or with floral patterns, which are super cute. Add a chunky ring or some bangles to complete your cute outfit. When it's time to do your makeup, go for a natural look.

How can I make Valentine's night special? ›

10 Ways to Make Valentine's Day Extra Special
  1. Celebrate Your Favorite Memories With a Photo Collage. ...
  2. Bake Their Favorite Treat. ...
  3. Create a Personalized Valentine's Day Card. ...
  4. Relive Your Favorite Date. ...
  5. Plan a Weekend Away. ...
  6. Turn Your Favorite Photo Together Into Digital Art. ...
  7. Volunteer Together for a Good Cause.

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.

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.

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