14 Valentine's Date Night Looks

Ah Valentine's Day, it's one of our favorite days out of the year. During winter, dressing for a candlelit dinner can be rough when you're concerned about the freezing temperatures and slippery sidewalks. Trying to look cute while also trying your best to stay warm doesn’t always go hand in hand but luckily, we're here to help! Valentine's Day dressing during chilly weather doesn't have to be a daunting venture; there are ways to look chic and sultry while still remaining warm and cozy. Look ahead to these 14 perfect winter date outfit ideas! 

Also, make sure to head over to our newest 90's Style Guide blog post, where we give you some major current and retro celeb style inspo!  




PSA: You don’t have to put your mini skorts away when it’s cold! A plaid mini like our Get A Clue Red Plaid Skort is always a classic, and you can always throw on a pair of tights for more warmth. Coordinate with our Carrie Grey V-Neck Crop Top and the Cece Black Vegan Suede Heels for an edgy winter fit. Major plus, this skort will also match that glass of wine you're sippin’ on with your date. 

Breathe some new life into your date night rotation by playing with texture. Pair some trendy vegan leather pants, like our Vertigo Black Vegan Leather Pants with the Flawless Black Lace Mesh Bodysuit and Holland Blue Colorblock Oversize Knit Sweater for a city-chic ensemble perfect for taking on date night! 

There's no better occasion for a wine-colored satin dress than on Valentine's Day! This satin dress always proves to be a versatile piece that's perfect on its own, or for staying warm by layering over tees and turtlenecks. Try layering this Demeter Wine Satin Mini Dress with our Charleston Black Turtleneck Sweater for an unexpectedly chic look. 


When in doubt, the classics always work! In this case, tuck our Signature Black Ribbed Turtleneck into your favorite dark-wash denim, like the Vertigo Black Vegan Leather Pants. Then, add a sexy pair of suede heels (we suggest the Cece Black Vegan Suede Heels) for a chic and effortless date night look! 

Looking for an understated outfit that doesn't scream Valentine's Day? Try still being festive with our High Energy Rust Sock Booties, and go for a monochromatic cozy-chic look with the Soul Mates White Turtleneck Bodysuit and Baby It's Cold Ivory Faux Fur Coat

If it’s a fancier occasion like dinner and drinks, this Maxine Wine Wrap Mini Dress will make you feel both gorgeous and confident for the night ahead. Throw on a faux-fur coat and heels (we suggest the Cece Gold Glitter Heels) to dress it up even further! 

This look is warm enough for cute early morning coffee runs with your beau, and trendy enough to meet up for late-night drinks! We love this super casual yet cozy look, all centered around our Baby It's Cold Mauve Plush Faux Fur Coat! Keep it simple underneath with the Carrie Grey V-Neck Crop Top and Get Ready Distressed Dark Wash Jeans

There's nothing that a knee-high boot can't fix. Whether you're pairing them with mini skirts or distressed jeans, our Follow Me Black Over The Knee Boots will give you the height you want for a late-evening dinner date this Valentine's Day. Pair these with our Clara Burgundy and Grey Plaid Skirt and our Luxe White Fuzzy Tank Top


Whether you're heading out for a casual date with your significant other, or to your go-to takeout spot, cozy and chic is ideal. With the right jeans and sweater, effortless dressing is achieved. Our Aleyna Blush Bodysuit styles so perfectly with the Little By Little Ivory Bubble Knit Cardigan and Cloud Nine Tan Booties to make the perfect casual date night look ever!

Just because it's cold outside doesn't mean you have to put away all your lace! Show off that gorgeous Sophia Black Lace Bralette by letting some lace peek out of our Carrie Grey V-Neck Crop Top. Keep your look casual with the Here We Go Distressed Dark Wash Jeans


Cozy lovers unite! The latest trend includes v-neck tees that show a bit of skin without risking warmth. For your next date night, pair the Carrie White V-Neck Crop Top with high-waisted jeans like our Ida Dark Wash Skinny Jeans for an elevated cozy look! Finish off your cozy look with our Alex Ruby Red Cardigan and Day By Day Natural Booties.  

Change up your typical Valentine's Day look with something new! Pair a crop tee like our Carrie White Crop Tee with the unexpected pant favorite of the season: vegan leather! We are so obsessed with the Vertigo Black Vegan Leather Pants, and we can't stop incorporating them into all of our outfits! 

Babes, we know more than anyone that in the dead of winter it’s hard to find the motivation to do anything other than bundle up in your favorite comfy joggers and watch rom-coms on repeat. So why not look cute while you're at it? We paired our Don't Sweat It Joggers with the Elise Dusty Coral Lace Bralette and Cecilia Blush Knit Sweater

You might think a turtleneck sweater isn’t dressy enough for a date, but you’ll be sophisticated and subtly sexy in our Charleston Red Turtleneck Sweater. Distressed jeans (like our Vanessa Medium Wash Distressed Jeans) make it more casual, while the Cece Black Vegan Suede Heels make it feel just dressed up enough!