The 15 Must-Have Outfits for Valentine’s Day

Every Valentine’s Day we end up asking ourselves, “What do I wear?” But not this year.


No matter what your plans are, these 15 outfits for Valentines Day have you covered! Besides, an occasion always feels a bit more special when you get to wear something new and exciting!


VALENTINE’S DAY OUTFITS FOR EVERY OCCASION

Whether you’re staying in, going on a romantic date, or enjoying a night out with your family or group of girlfriends, ensure you'll be celebrating Valentine’s Day in style. Find your perfect Valentine’s Day dress or jumpsuit in our style blog below. Then shop all of our outfits for Valentines Day in the Date Night Dresses & Jumpsuits collection to make it yours!


While a classic Little Black Dress is a wise choice, mixing it up with beautiful floral prints and bold colors also works well for this holiday. Check out our featured date night cocktail dresses and special occasion jumpsuits below. These looks stay true to the romantic spirit of Valentine’s Day 2020, while pops of pink and red make these pieces perfect for standing out on a regular Wednesday or at the office. 

romantic date night

The key to finding the perfect Valentine’s Day date outfit is simplicity. With so many perfect outfits for Valentines Day available, you’ll want to look for styles that make you feel sexy, but not risque or out of place.


Everything about Amber screams "I know I look good and I feel good." Amber’s above-the-knee slit and sheer sleeves allow you to show off a little extra skin with class. You’ll look both daring and sophisticated on your romantic Valentine’s Day date night.

Uptown is the ultimate romantic date night jumpsuit. Made from stretch jersey knit and featuring a draped cowl neck and waist tie, this foiled metallic jumpsuit is chic, sophisticated, and comfortable. It’s the perfect choice for a Valentine’s Day dinner at an upscale restaurant!

Lisa is a Connected Apparel staple. Our tried-and-true silhouette flatters women of all shapes and sizes. This faux wrap dress features a red metallic embroidered bodice and lightweight stretch skirt. Lisa is the perfect date night dress for feeling comfortable while looking like a million bucks.


The jumpsuit itself is SASSY! The cut itself is generous and it flatters the areas that I appreciate about my body and skims the areas that need work… Love, love, love it. I highly recommend [the Uptown] jumpsuit!


casual date night

Not all outfits for Valentines Day are created equal. While a flirty Amber floral print dress is perfect for a romantic date night, casual dates require an outfit more lowkey. Dates to a coffee shop, café, or out for ice cream warrant a look that is cute, stylish and simple.


Want to know the best-kept secret for looking effortlessly sexy? Dress down something ultra flirty and feminine—like our Natalie floral dress. Natalie’s slinky material glides over your body and will keep you feeling comfortable all night long. Pair Natalie with a simple denim jacket and let her curve flattering ruffles take you from uptown fancy to downtown fabulous.

Kennedy is refined sophistication. Our version of the classic Little Black Dress, Kennedy is extremely versatile and makes an ideal choice for any type of casual Valentine’s Day plans. 

Tonya is a timeless midi dress that moves with you. The draped cowl neck and side ruching beautifully compliments all shapes and sizes. And even though your Valentine’s Day plans call for casual date night attire, the metallic gold fabric accents create eye-catching sparkle without feeling formal.


I love this dress. It arrived quickly...It will also be perfect for any Holidays events that come up.


desk to dinner date

Heading out straight after work? Or planning a casual, low-key evening? When you’re browsing outfits for Valentines Day, you’ll want a dress or jumpsuit that can take you from desk to dinner without a hitch.


Harlow is one of our favorite day-to-night dresses. The structured neckline and tailored body create Harlow’s iconic workwear silhouette. But it’s the stretch floral fabric that makes this dress comfortable enough to wear all day and night long. Simply put, your Valentine’s Day outfit will exude sophistication and feel fabulous.

The ultimate desk to dinner piece, Bri is an all-black jumpsuit made from stretch crepe scuba and designed with feminine chiffon sleeves. Bri is the way to go when you’re looking for a chic alternative to a traditional Valentine’s Day dress.

The Lisa is the perfect all-around desk to dinner dress. Whether you and your significant other are having dinner at home or heading out to a favorite restaurant, Lisa looks beautiful with or without a reservation. Trade your boardroom pumps for strappy sandals. And swap the briefcase for bangles. The Lisa dress makes it so easy to transition from work to date night.


I love this dress. It fits well, is true to size and is very flattering.


date night with friends

What would we do without our BFF? If you’re spending a laidback Valentine’s Day with friends, a light, casual dress or versatile jumpsuit is a great option.


She's versatile. She's fun. She's Janis. Her simple trapeze shape creates balance to the high-low ruffle detail on the sleeves. And the bold floral print makes her the perfect dress to accompany a fun Valentine’s Day with friends.

Gloria is everything you want in a jumpsuit. Her cold shoulder chiffon sleeves and in-set waist are the perfect flirty compliments to wherever the night takes you!.

Sasha is the above-the-knee dress that’s sure to turn heads! An A-line silhouette, this floral print dress features raglan sleeves for a unique and flirty feel. It’s the perfect dress for a Valentine’s Day with friends that carries on late into the night.


Transitions well [from] day to night, dress up or down.


family date night

Keep it low key and stylish while spending Valentine’s Day with your family, so you can maximize the time you spend together.


Julia is a modern twist on the classic drop waist dress. Perfect for a busy family’s TBD Valentines Day plans, you can easily dress Julia up or down and be ready in minutes! Add a red accent purse or earring to stay subtly on-trend for a tonal Valentine’s Day 2020.

Sunny proves you don’t have to choose between looking fabulous and being modest. Ruched side seaming helps deter any pesky skirt ride-up, while the breezy v-neck flounce adds lovely additional coverage. Sunny is the perfect fun and feminine dress you can slip-on in a breeze and feel comfortable in from early morning carpool to evening family date night.

Sara is a timeless jumpsuit that’s perfect for a more formal family date night. A chiffon crossbody ruffle adds dimension, movement and an extra level of sophistication. With the perfect pair of heels and chandelier earrings you’ll be ready for a beautiful family gathering on Valentine’s Day.


This [dress is] great quality…The product also came very quickly, which was also great! I very much recommend this product and this company!


On Valentine’s Day, there are as many outfit options as there are creative date choices. Every different plan for a V-Day date calls for a slightly different dress code, so deciding what to wear on your’s can be understandably difficult.


Use this guide to match your upcoming date with the perfect outfit. Then shop our collection of gorgeous outfits for Valentines day. And make that dress or jumpsuit yours! Rest assured that you’ll feel comfortable and confident this Valentine’s Day and shop now.

get 20% off!


Tell us what your favorite Valentine's Day 2020 outfit is in the comments below & we’ll send you a 20% off promo code to use for a date night outfit! 

1 comment

I love the Lisa Red Dress, is my favorite old fashion, about, sleeve and length.

Yolanda R. Sanchez February 13, 2020

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