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

Table of Contents
The Pioneer Woman Flounce Sleeve Dress The Pioneer Woman Flounce Sleeve Dress A-Line Swing Midi Dress A-Line Swing Midi Dress The Pioneer Woman Tiered Ruffle Dress with Long Sleeves The Pioneer Woman Tiered Ruffle Dress with Long Sleeves Chenille Sweater Dress with Belt Chenille Sweater Dress with Belt Express High Waisted Satin Side Slit Midi Skirt Express High Waisted Satin Side Slit Midi Skirt Heart Relaxed Everyday Shirt Heart Relaxed Everyday Shirt The Pioneer Woman Square Neck Blouse with Ruffle Sleeves The Pioneer Woman Square Neck Blouse with Ruffle Sleeves Chiffon Bell Sleeve Blouse Chiffon Bell Sleeve Blouse Honeydew Star Seeker Pajama Set in Black Heart Honeydew Star Seeker Pajama Set in Black Heart Howdy Valentine Graphic Tee Howdy Valentine Graphic Tee Burgundy Cable Knit Turtleneck Sweater Dress Burgundy Cable Knit Turtleneck Sweater Dress Mauve Turtleneck Sweater Dress Mauve Turtleneck Sweater Dress Red Sleeveless Wide-Leg Jumpsuit Red Sleeveless Wide-Leg Jumpsuit The Pioneer Woman Keyhole Blouse The Pioneer Woman Keyhole Blouse Alex Evenings Embroidered Dress Alex Evenings Embroidered Dress The Pioneer Woman Blanket Cardigan Sweater The Pioneer Woman Blanket Cardigan Sweater Heart Jacquard Bias Midi Skirt Heart Jacquard Bias Midi Skirt Mock Neck Tiered Mini Dress Mock Neck Tiered Mini Dress Cue Wrap Long Sleeve Dress Cue Wrap Long Sleeve Dress Wrapped Up In Love Mauve Satin Faux-Wrap Midi Dress Wrapped Up In Love Mauve Satin Faux-Wrap Midi Dress

You'll fall in love with these ideas! šŸ˜

By Macie Reynolds
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 littleā€”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 pantsā€”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

Bestseller

The Pioneer Woman Flounce Sleeve Dress

These Cute and Comfy Valentine's Day Outfits Are Perfect for Any Date Night (3)

1

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.

2

3,800+ Reviews

A-Line Swing Midi Dress

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

2

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!

3

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 (5)

3

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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4

Several Colors Available

Chenille Sweater Dress with Belt

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

4

Several Colors Available

Chenille Sweater Dress with Belt

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.

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.

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

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

Now 41% 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.

8

3,000+ Reviews

Chiffon Bell Sleeve Blouse

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

8

3,000+ Reviews

Chiffon Bell Sleeve Blouse

Now 25% 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!

9

Coziest Pick

Honeydew Star Seeker Pajama Set in Black Heart

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

9

Coziest Pick

Honeydew Star Seeker Pajama Set in Black Heart

Who says you canā€™t dress up for even the most casual Valentine's Day at home? The pretty pink hearts on this PJ set make it perfect for a rom-com movie night.

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10

13,000+ Reviews

Howdy Valentine Graphic Tee

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

Time to sweeten up your styleā€”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.

11

Comfiest Find

Burgundy Cable Knit Turtleneck Sweater Dress

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

11

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.

12

Relaxed Vibes

Mauve Turtleneck Sweater Dress

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

12

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.

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13

Gorgeous Color

Red Sleeveless Wide-Leg Jumpsuit

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

13

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.

14

Ree's Style

The Pioneer Woman Keyhole Blouse

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

14

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!

15

For an Extra-Special Date

Alex Evenings Embroidered Dress

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

15

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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16

Bestseller

The Pioneer Woman Blanket Cardigan Sweater

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

16

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.

17

Pretty in Pink

Heart Jacquard Bias Midi Skirt

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

17

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.

18

Just Fancy Enough

Mock Neck Tiered Mini Dress

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

18

Just Fancy Enough

Mock Neck Tiered Mini Dress

Now 35% Off

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

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19

Best Dress

Cue Wrap Long Sleeve Dress

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

19

Best Dress

Cue Wrap Long Sleeve Dress

No matter the occasion, you can't go wrong with an LBD. Featuring a universally flattering a-line wrap style made of organic cotton with pockets, it's easy to love and even easier to style.

20

Several Colors Available

Wrapped Up In Love Mauve Satin Faux-Wrap Midi Dress

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

20

Several Colors Available

Wrapped Up In Love Mauve Satin Faux-Wrap Midi Dress

What is it about satin that's so darn romantic? Here, sleek fabric meets cascading ruffles and a tie waist for a tailored-yet-carefree look.

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)
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