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
          ALEJANDRA ALONSO ROJAS Silk Satin Tank Gown
          Hugo in Black Embossed Croc
          Emme Parsons Hugo in Black Embossed Croc
          Gerwig Blazer in Black
          Rachel Comey Gerwig Blazer 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
            BOTTEGA VENETA Henley Oversized Sweater
            Beacon Jean in Mid-Blue Wash
            MERLETTE Beacon Jean in Mid-Blue Wash
            Square-Toe Mary-Jane (Margot Mary-Jane)
            VIVAIA 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 sheer tights, statement earrings, and sleek heeled boots,” says Milton. “This look will keep you cozy, yet sexy.”

            Camira Mock Neck Sweater
            BY MALENE BIRGER Camira Mock Neck Sweater
            Cami Boot
            STAUD Cami Boot
            Now 52% Off
            Croco Swipe Bag
            COPERNI 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
            Totême Raglan-Sleeve Croco Coat
            Turtleneck Black
            WARDROBE.NYC Turtleneck Black
            Elastic Waistband Jean in Denim Washed Black
            MERYLL ROGGE 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
            AISLING CAMPS Isabella Turtleneck Cashmere Sweater
            Leather Culottes in Black
            PROENZA SCHOULER WHITE LABEL Leather Culottes in Black
            Indre Bow in Alabaster
            GIGI BURRIS 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 sheer pair of tights, knee high boots, and an oversized cream colored sweater.

            Amaya Cashmere Turtleneck Sweater
            Nili Lotan Amaya Cashmere Turtleneck Sweater
             Sequined miniskirt
            SELF-PORTRAIT Sequined miniskirt
            Square Toe Boot
            VICTORIA BECKHAM 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
            LORO PIANA Ribbed-Knit Off-Shoulder Cashmere Sweater
            Regular Fit Jeans
            Blumarine Regular Fit Jeans
            Condor 2 Sneaker
            VEJA 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 Lisa Yang fits the bill. The knit construction gives off a slightly relaxed feel while the gold embellishments, on the bag, adds a touch of refinement.

            Ember Vest in Sand Boucle
            Lisa Yang Ember Vest in Sand Boucle
            Kael Skirt in Sand Boucle
            Lisa Yang Kael Skirt in Sand Boucle
            Wander Matelassé Mini Hobo Bag
            MIU MIU 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
            THE SLEEP CODE Washable Silk Short PJ Set
            Terrycloth Robe
            FLEUR DU MAL Terrycloth Robe
            Wintercozy Cashmere and Silk Slippers
            LORO PIANA 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
            LOULOU STUDIO Movas Blazer Black
            Alma Skirt Min
            DL1961 Alma Skirt Min
            Pure Matt 50 DEN Women Tights
            Falke Pure Matt 50 DEN Women Tights
            Now 37% Off