Cute as a Cupid – 15 Fantastic Valentine Day Outfits

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Whether you and your Romeo have planned a night on the town, dinner and a show, party with friends, or a 4-star night in, we’ve got the looks sexy enough to make Cupid drop his bow.

It can be fun and flirty or chic and classic, or a bit of both. Ready to dive in?

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DINNER FOR TWO

Reservations for two? Dining out for Valentine’s day has always been a popular tradition, and this year we’re really seeing a return of the reservations. So if you and your loved one are heading out, make it a truly fun occasion with dressing your best!

This sorbet-inspired fit combines sweet pastels and mixed metals to create a feast for the eyes. We start with Windsor’s ruched, sweetheart neckline mini dress (EDITOR’S NOTE – Want this dress today? Windsor has over 325+ brick and mortar stores across the country. Just input your zip code to find the store nearest you!).

Next, we accessorize it with M. Gemi’s silver pumps and your own personalized initial necklace from Zoe Lev (in 14k white gold). Then to keep things from going too monochromatic, we mix things up with a champagne satin clutch from Nina, and finally Rina Limor’s confectionary-colored gemstone earrings in warm rose gold.

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Profess your love…for regal velvet…in this next fit. This deep burgundy beauty from DB Studios has plenty of ruching that just adds more visual interest already created by the romantic floral pattern. We keep that romance going with Sophia Webster’s absolutely gorgeous gold sandals, Windsor’s heart-shaped clutch (comes with a chain if you prefer crossbody) and RockFlowerPaper’s double pendant necklace. Of course why stop the sparkle there? A pair of starburst gold hoops from Sterling Forever will give your lobes that finishing touch.

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Craving only new season stuff? Here’s a coquettish fit, starting with a cheeky lip pattern from Diane von Furstenberg’s newest season of wrap dresses. Pair this silk-jersey mini with some lush, new season velvety Jimmy Choo’s and Mansur Gavriel’s M Frame bag from their spring line. Accessorize with Kendra Scott’s gold and pink magnesite necklace (from the 2023 Valentine’s Day collection) and Mondo Mondo’s new season Diva ring.

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Consider this next fit your Valentine’s day power suit. Elie Tahari’s sumptuous red velvet blazer and wide leg pants take things to boss level with La Perla’s pretty pink cami. Add Joomi Lim’s Queen necklace (because you are) and Joie’s burnished gold mules complete the look.

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Finally, if your loved one is pulling out all the stops, you should too! Upscale dining is the perfect excuse for going extra, and this full-length, velvet gown from Bariano in haute pink drips trendy chic. Building on the luxe, we add a three-row pearl necklace by Kenneth Jay Lane and matching garnet drop earrings from Gem & Harmony. All that’s left is to slide into some black velvet sandals from Veronica Beard, grab our Liu Jo clutch and we are ready for aperitifs.

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DINNER & A SHOW

Grabbing a bite to eat before seeing your favorite artist, hitting the club or taking in a great comedy show? You’ll want a fit that works well for both venues. We’ve got your inspo right here.

Here’s a concert-ready look that can go from casual dining to dancing in zero time. Windsor’s appropriately named Dance With Me crop top works a combo of pulse-rising red with beaded fringe that’ll sway with every beat. Looking for something to smooth your front and give your booty a little boost? NYDJ’s faux leather straight pant from their Sculpt-Her collection does just that. To keep those toes tapping, M. Gemi’s Cristina bootie has just the right amount of heel (Editor’s Note: for the record, when matching boots to leather pants, suede plays better than patent or grain leathers). For accessories, we’ve got Eye Candy LA’s multi-colored statement drop earrings and just for fun, a aughties-celeb inspired rimless pair of light tinted sunnies that won’t leave you heartbroken if you lose them at the event (they’re only eight bucks!).

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Hitting the club with your Bae means getting your glam on. This silky romper from Versona in plumy mauve doesn’t disappoint. And while you’re showing off your best moves, these long draping rhinestone earrings from Baublebar will really bring the bling. Nina’s chocolate-burgundy slingbacks are a sexy mid-heel meant for moving. Last touch, Chiara Ferragni’s new season belt bag is a show-off all it’s own (you can wear it crossbody or on the waist).

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When the dance floor gets hot, we go hotter (as in hot pink). With an A-line skirt that will twirl with you as you move, we’re loving this dress by Jules and Cleo. Keeping the bling going, we add some sweet candy-colored crystal earrings and some rhinestone sandals (in wide width for extra comfort). As for your bag, we’re all about the feathers! This lipstick red, feathered clutch by Serpui is an investment piece you’re sure to use for all your upscale events.

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When moving between destinations, it’s nice to have a one-and-one outfit. Lulus sequined jumpsuit in deep red will keep you mobile and looking amazing. Speaking of mobile, Larroude’s new season of kitten heel, the Valerie XX is bold, beautiful but won’t have your feet aching after a night out. A deep burgundy Marc Jacobs bag is big enough to keep your essentials. And of course, Valentine’s day is the day for the heart-shaped jewelry, so we go big with Zadig & Voltaire’s massive cuff and Eye Candy LA’s statement drop earrings.

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The spotlight might be on the stage, but all eyes will be on you as the enter the room in this fit. Halston’s deep garnet red dress with plunging keyhole top is truly a showstopper. Playing on the darker hue, we paired this sequined beauty with a chocolate-toned glitter clutch from Jimmy Choo and Nina’s choco-burgundy heeled sandal. Of course a dress this amazing needs no jeweled accessories, but hey, this is Valentine’s day! So from Baublebar, we pull these heart-shaped mega-hoops to complete the look.

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PARTY WITH FRIENDS

Celebrating with friends for the holiday? Whether is for Galentine’s or Valentine’s, give your look a little holiday lift with an outfit that playfully embraces the day.

Here’s a great example that’s perfect for a chill party with friends. We start with a comfy mock turtleneck sweater from Sugarlips with definitive Valentine vibes. Pair this with Mott & Bow’s equally cool-casual Charlton jeans that score big points with their easy fit and even bigger points in their eco-friendliness (they’re made from hemp). Zoe Lev’s adorbs initial stud earrings in 14k gold add a flash of personalized bling. Pulling from adidas’s new season of ultraboost sneaks, the limited edition Violet Fusion are covered in colorful lavender hearts, and then we round things out with one of our editors favorites – Dagne Dover’s neoprene fanny pack, made from recycled plastic bottles.

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Get your flirt on with this next fit, which checks the boxes for casual and cute. Rag & bone’s spliced midi skirt shows a little leg while a Jacquemus barbiecore cropped sweater amps things up, with Mott and Bow’s super soft tee underneath. An adorbs heart-hand necklace from Gem and Harmony adds a sweet touch, especially when paired with a heart crossbody from Tous. Last but not least, slide into a pair of Neena flatform sneaks by Circus NY and let the festivities begin.

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Here’s another great fit for a group get-together. We start with a pair of soft suede velvet jeans from Paige in rosy pink and some beefy silver earrings from Tous, shaped like hearts (‘natch). Adding to the romantic feel, we have The Kooples sheer puff sleeve top with rag & bone’s rib tank underneath. Of course we’re all friends here, so we round out this look with a pair of vintage-inspired high tops from Clarks in dusty gray.

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For a look that’s quick and cute, grab a pair of this season’s must haves – the cargo pant – and pair it with a few fun elements, like Red Bubble’s glitter lips tee and Nina’s tiny-but-mighty heart studs. Finally, keep things kicking with a true classic, the Air Jordan 1 in red/gray low.

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If you’re not into heavy amounts of pink and red, this last fit is perfect for you. A fun ditzy floral dress, combined with Circus NY’s velvety platform booties gives off plenty of romance vibe without dipping too far in the crimson zone. Of course, adding in a little emoji fun, courtesy of Alex & Ani and a heart-shaped multi-colored bag from Kurt Geiger brings in the spirit of the holiday.

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