Cute as a Cupid – 15 Fantastic Valentine Day Outfits

Whether you and your Romeo have planned a night on the town, a 4-star night in, or making it a night of Remote Romance, we’ve got the looks sexy cool enough to make Cupid drop his bow.


With outdoor dining and indoor eating (with restrictions) in many areas now allowed, Valentine’s Day is the perfect excuse to indulge in a socially-safe, sexy dinner rendezvous with your S.O. Feeling a little fashion paralysis? We got you, with five fantasy-inducing outfits sure to satisfy…

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Our first outfit is velvety smooth, thanks to Windsor’s Heart of Glam Mini-dress ($39.90). We add some fun bling with Haloed Asscher’s Erin Drop Earrings ($68) and a dark crimson slingback courtesy of Nina’s Shoes ($54.50). A heart-shaped red glitter cloth mask from Red Bubble ($10) keeps you safe until you hit your table and all is complete with none other than a baby pink Croc Four Ring Flat Clutch by Alexander McQueen ($1,790)

This next outfit will bring a twinkle to your eye, with tons of tiny rhinestones that have been heat applied onto this plus-size Windsor Arielle Midi Dress ($34.45). Why not keep the constellations going then, with a complementary Heat Stone Face Mask ($12.90). Add some fun accessories such as Senso’s black velvet Melvy IV Heels ($139), fun angular Cutout Triangle Pearl Stud Earrings from Joomi Lim ($42) and last but not least carry your own silver lining cloud with Mansur Graviel’s Mini Cloud Clutch ($495).

It’s been a while since we’ve been out and about, so why not go full-on Flirt? A baby pink Faux Leather Cropped Top ($36.90) is the perfect combo with this creamy, super fuzzy Trendy Babe Knit Mini Skirt from Windsor ($19.00). Take your cat’s meow of an outfit to next level with a black satin face mask called Purrfect ($9.90). Finish with some equally awesome Disco Metallic Sandals from Oscar Tiye ($259) and show ’em you’ve got heart with Baublebar’s Gerwyn Drops ($42) and Marc Jacob’s Heart Crossbody Bag ($270)

If the typical bright reds of Valentine’s Day isn’t quite your thing, try dipping into something darker, like this luscious wine-colored, Plus size velvety number from Windsor ($24.45). Keep the sparkle going with silver metallic sandals from kate spade new york ($55.99), some “go big or go home” Silueta Heart Earrings from Tous ($169) and Tosca’s Silver clutch with resin chain ($88).  And you certainly won’t forget your mask with this sequined lovely from Karl Lagerfeld Paris ($35)

For our last “Going Out” look, we get a little punky but still look sweet. Start with Rose Darling Floral & Lace Mini Dress ($32.90) and simpatico Floral Velvet Face Mask ($8.90). Then kick things into high gear with Sam Edelman’s tall lug boots ($120) and Simone Rocha’s asymmetrical Red Mini Drip Earrings ($175). Finish the look off with Coperni’s hole-in-the Heart Shaped Clutch Bag ($678).



With so many things still uncertain, lots of folks are opting to continue with holiday celebration from home. And why not? No reservations or masks required, and bonus – you get to be as dressed up or dressed down as you like, though TBH what’s wrong with getting a little glammed up?

How perfect is this ensemble for dressy-cazh? The silky, lipstick red Deep Cowl-Neck Blouse from Boston Proper ($39.98) adds instant luxe and is the perfect frame for Italian Silver’s delicate Heart Necklace ($69.99). Heart printed Palazzo Pants by DoubleJ ($298) look dressy but are actually as comfy as your fav sweats. And of course, if we’re talking comfort, these super-fuzzy, faux shearling slides from M.Gemi in Blush ($198) are just what the podiatrist ordered!

Double down on the sexy factor with the seductiveness of lace and cherries. Windsor’s Living for Lace Bodysuit ($29.90) pairs perfectly with Bebe’s Lace Detail Black Wash Skinny Jean ($119).  So in turn, does Eye Candy Los Angeles’ CZ Cherry Earrings ($29.99) match with NARS new Air Matte Lip Color in Power Trip ($26.00). Comfy couture Heart Strap slides by Giuseppe Zanotti ($375) complete the look.

Everything’s coming up roses with this look. A gorgeous, Plus Size Floral Dress from Shein ($19.00) sets the mood, followed by, appropriately enough, Alex and Ani’s True Love Statement Earrings ($40.60). But remember we’re dining in? So skip the blister-inducing heels and add a zing of color pop with Birkenstock’s Barbados EVA Slides in hot pink ($51). Don’t forget to leave them wanting more, with as little spritz or two of award-winning Amazing Grace by Philosophy ($52).

Embrace your inner at-home Diva this Valentine’s Day. Start with this burgundy velvet Tie Waist Cat Suit by Windsor ($16.97) and keep the velvet coming with Joomi Lim’s Crystal Charm Velvet Choker ($104). Sol Sana’s sweet baby pink Parlix Slides ($95) are the perfect vehicle to show off some Rouge Matte Nail Colour by Christian Louboutin ($57).

Our last holiday-at-home outfit is both comfy and couture. We start with a creamy, blushing Puff Sleeve Crew Neck Sweater from Nicole Miller ($135) and juxtapose that against a silvery satin Pleated Skirt from Shein ($20). And speaking of comfy, these day slippers from Aquatalia called Rayla ($350) are like frothy cappuccinos for your feet. Finally Tous’ lovely Long Rose Vermeil Silver Statement Earrings ($357) are the icing on this tasty treat of a fit.


Whether by choice or necessity, the pandemic has, for many people meant having to share time with loved ones online…and that includes even romantic ones. If your Valentine will be on the other side of the keyboards this year, that’s no reason you can’t still have some fashion fun. Here’s a few coquettish but comfy options your Valentine is sure to like…

Why not start with giving your lover a little lip? This front-and-center Pucker Up Graphic Tee by Windsor ($19.90) is camera ready for your waist up convo. Show your lobes a little love too with Baublebar’s Be Mine Cupid Earrings ($44). And since we’re talking a sitting engagement, these Valentine’s Day Red Heart Leggins from Designer Studios ($59.95) and Love Moschino Heart Logo Slides ($140) are sweet and stylish.

Take a cue from those classic Valentine’s Day heart candies and dip into some dreamy pastels. Algo Yoga’s Parisian Pink Twist Top ($68) will look fantastic when paired with Isabel Lennse’s Heart Embellished Drop Earrings ($133). Grab some Hearts Jogger Pants from Splendid ($34.24) and some Neon Accented Slide Sandals from Nautica ($19.99) for some easy chilling vibes.

Are you a bit of a wild child? Why not show it off with Chaser’s Wild At Heart Cropped Sweatshirt ($39.99). Let ’em know they still have your heart on lockdown though with Sphera Milano’s Pave Padlock Earrings ($39.99) and Ultracor’s Sprinter Lux Heart Leggings ($229.99). Finally, keep your paws cozy by slipping into Aquatalia’s Emilia Shearling Slip Ons ($295).

This outfit is sure to give them the ‘skinny’ on your thoughts. We start with super dark Mott & Bow’s High Rise Skinny Jane ($108) and go full on playful with Comme Des Garcon Play’s Heart Eyes T-shirt ($107), Amir Slama’s Heart Earrings ($89) and adidas Superstar Bold Shoes ($110) which are embossed with the cutest little red hearts!

We think our last outfit is pretty “Marvel-ous”. If you and your S.O. share a love for the Marvel movies, they’ll definitely appreciate this Marvel Licensed Avenger’s Endgame Tee with Iron Man’s Quote “I love you 3000” ($30). Punctuate your feelings with these additionally adorable Be Mine Sweetheart Hair Clips from Etsy ($4). Then keep your casual with some pretty Floral Contrast Leggings from Bebe ($98) and these downright snuggly Fluff Ya Slides from Uggs ($79.99)

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