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

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

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.

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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.

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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.

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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.

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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."

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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.

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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? ›

If you're going out but want to keep things more low-key, Gulbransen suggests pairing your favorite pants or jeans with a Valentine's Day-inspired blouse or sweater. Or, you can up the ante and try a fun pair of red trousers.

What is the perfect date outfit? ›

For women, go with a little black dress or a casual blouse and jeans finished with feminine accessories and a natural makeup look. Stick to solid colors or small-scale prints and avoid anything with loud patterns and obnoxious colors that may distract your date.

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?

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 best color to wear 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.

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.

How to dress for a date female? ›

A midi-length dress and strappy heels are perfect for a dinner date. A strappy floral dress will go well with sandals if you are headed to a park. A casual sport fit is perfect for a sporty activity like bowling. A crop top and a pair of jean pants are perfect for a club date paired with sneakers and a sling bag.

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 do you look classy on a date? ›

If you are going to a fancy restaurant, wear a nice dress or a nice pair of pants and some respectable shoes. If you are just going for a walk in the park, wear something nice but casual, such as a top, pants and a belt. Since this is the ultimate non-gendered look, it's a perfect solution for all events really.

How to look hot on Valentine's Day? ›

Try a classic, fancier look with a long crimson gown, or have fun with a low-key hot pink sweater and jeans.
  1. Craft a monochromatic outfit, like head-to-toe blush tones, for an on-trend Valentine's Day look. ...
  2. Shake things up by going monochromatic but with different shades of the same color.

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

Pair a light pink dress with bright red tights, or style a bold red top with cute pink pumps! If you're looking for Valentine's Day outfit ideas that are a bit more sophisticated (February 14th does fall on a work day, after all!), tone the look down with a black blazer, sleek black boots, or a neutral sweater.

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.

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 not to wear on a dinner date? ›

While some of us tend to look overly sexy on a first date, others tend to be way underdressed. Even if you have a bikini-ready body, do not wear leggings, a hoodie, or your worn-out sneakers on your first date. You'll give the impression that you have no interest in putting forth the effort to look nice.

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.

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 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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