10 Valentine’s Day Outfits for Any Occasion

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Love is in the air, and as such, those of us who are planning to exchange flowers and boxes of chocolate on February 14th are also beginning to ruminate on how we’ll spend that special day with that special someone. Perhaps an evening of drinks and dinner at a lavish restaurant? Or maybe a daytime date at a coffee shop or a museum? No matter what option we settle on, we’re still stuck with the critical question of what to wear. And because this question yields multiple answers, not only is love in the air, but so is stress.

To ease your Valentine’s Day-related anxiety, we’ve called on Glamhive stylists Georgia Milton and Kasia Michaels to help you pick the perfect outfit. “The best type of outfit to wear on Valentine’s Day is something that makes you feel true to yourself and comfortable, as this will help you to live more in the moment,” says Milton.

Ahead, you’ll find endless Valentine's Day outfits for any occasion, whether you prefer to stick with quiet luxury pieces that will fit nicely into your capsule collection or you would rather push the boundaries with trendy statement colors.

For a classy dinner:

“For a memorable dinner date, opt for a classy and romantic outfit,” says Michaels, who suggests wearing a red silk dress to bring a sense of allure to your look. If you decide to go this route, your red dress will undoubtedly be the standout element of your ensemble, so make sure to accessorize with neutral pieces.

Silk Satin Tank Gown

Hugo in Black Embossed Croc

Axel Coat in Black

For a daytime coffee date:

If you’re planning to keep Valentine’s Day casual this year, take a visit to your local coffee shop. For this type of occasion, Michaels recommends a versatile outfit that offers comfort. “Last season's runways offered many 'normcore' look ideas that could serve as inspiration,” says Michaels. “Consider an ensemble like an oversized red Bottega Veneta sweater, a white crew neck tee, '90s pinch waist straight jeans, and Mary Jane flats for a chic yet relaxed vibe,” she adds.

Henley Oversized Sweater

Beacon Jean in Mid-Blue Wash

Square-Toe Mary-Jane (Margot Mary-Jane)

For a night at a cocktail bar:

Cocktail bars are often moody and dimly lit. To match the ambiance, lean into warm hues like shades of beige and brown. “Go for something like a long sleeve knit dress and complete the look with transparent tights, statement earrings, and sleek heeled boots,” says Milton. “This look will keep you cozy, yet hot.”

Camira Mock Neck Sweater

Cami Boot

Croco Swipe Bag

For a night at the movies:

Dressing for the movies is simple, so try not to overthink it! Easier said than done, of course, but we would recommend wearing a turtleneck, a pair of jeans, and a coat that spices up the outfit a bit, like this croc-embossed treasure from Totême.

Raglan-Sleeve Croco Coat

Turtleneck Black

Elastic Waistband Jean in Denim Washed Black

For a game night:

Make game night even more enjoyable by adding a trendy undertone to an effortless look. “Valentine’s Day is such a great opportunity to have some fun with your style, especially since it’s in the dead of winter and getting dressed might not feel very inspiring,” says Milton. “Bows are everywhere right now, and a bow in the hair could liven up a whole look.”

Isabella Turtleneck Cashmere Sweater

Leather Culottes in Black

Indre Bow in Alabaster

For a wine night:

Sip on a glass of sparkling wine while wearing a sparkly skirt. “My favorite way to style something like this is to let it be the most exciting part of the look, and let everything else support it,” says Milton. To follow Milton’s guidelines, wear Self-Portrait’s sequin mini skirt with a transparent pair of tights, knee high boots, and an oversized cream colored sweater.

Amaya Cashmere Turtleneck Sweater

Sequined miniskirt

Square Toe Boot

For a stroll in the museum:

A museum is the perfect space for two art connoisseurs, and even if you wouldn’t classify yourself as a bona fide aesthete, you can still enjoy a casual stroll. As for what to wear, a laid-back look will do just fine. “I would try a chunky oversized sweater that effortlessly drapes off the shoulder paired with jeans and a fun sneaker,” says Milton. “Finally, to complete this casual look, a pair of hoops can be the cherry on top,” she adds.

Ribbed-Knit Off-Shoulder Cashmere Sweater

Sammy Jeans in Azure

Condor 2 Sneaker

For a Galentine's Day brunch:

No partner? No problem. Take your closest girlfriends out for a celebratory Galentine’s Day brunch. Since a fun brunch outting typically involves blending casual and classy, we believe this set from Miu Miu fits the bill. The knit construction gives off a slightly relaxed feel while the gold embellishments, on both the set and the bag, adds a touch of refinement.

Wool Knit Cardigan

Wool Mini Skirt

Wander Matelassé Mini Hobo Bag

For an evening at home:

Sometimes the best Valentine’s Day date is spent indoors. Cuddle up on the couch and turn on a classic '90s rom-com. Dress for the occasion in pink pajamas, a cozy robe, and a fuzzy pair of house slippers.

Washable Silk Short PJ Set

Terrycloth Robe

Wintercozy Cashmere and Silk Slippers

For the theater:

A night at the theater calls for a sophisticated outfit. If you’re not sure what to wear, one of the easiest ways to formulate a look is to identify a trend that you’d like to try out, and work around it. “Playing with trends is a fun way to experiment with your style and I always encourage my clients to take risks if they feel tempted,” says Michaels. “For instance, embracing the red tights trend instead of going all red for the evening can be a striking choice,” she adds. Complete the look with an oversized black blazer, a sleek mini skirt, and a pair of Saint Laurent patent high heels.

Movas Blazer Black

Alma Skirt Min

Embellished mesh tights

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