Outfits Inspired by Various Types of Romance

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The season of love is upon us! Whether you’re busy assembling Valentine’s Day outfits or ignoring your

ex’s messages by reaching for your gua sha massager, chances are that love is on your mind. Instead of revisiting the amateur poetry you wrote over a bad breakup or indulging in a film marathon of romantic tearjerkers, dream a little with this style guide inspired by various romance scenarios.

With a nod to the silver screen, I’ve assembled seven cute outfits inspired by a range of romantic situations, whether it’s a meet-cute at the pizzeria or an epic breakup over cocktails. It probably won’t bring you the perfect Valentine’s Day, but it might get your creative juices flowing when revamping your wardrobe for future dates or just for strutting about town!


Indesi – Pink Tie-Dyed Tee | Omelia – High-Waist White Jeans | SouthBay Shoes – White Sneakers
Vonluxe – Butterfly Ring | Show Mind – Mesh Scrunchie | iswwas – “Indigo” Series 2022 Hardcover Diary

From meet-cutes at the school hallway to that longed-for first kiss, first love is the stuff of rom-com dreams. Feeling emotional from the memories? There’s no need to dig out your teenage diaries. Capturing the sugar rush of your first date, this look radiates girl-next-door vibes along with a healthy dose of sass. A perfect outfit for weekday hangouts at the ice cream parlor or lazy Sundays at the park, this ensemble comes in a simple, breezy silhouette with offbeat details, like heart cut outs and textured fabrics. A pair of sleek white sneakers seals the deal, while a butterfly-shaped ring and mesh scrunchie up the fresh-as-a-daisy vibes.


chuu – Slim-Fit Turtleneck Top | FROMBEGINNING – Plaid Corduroy Overall Dress | chuu – Eco-Fur Jacket
KATENKELLY – Rose & Pearl Earrings
| Jamfune – Geometric Ring | JUSTONE – Block-Heel Ankle Boots

Let’s face it, we’ve all had the bittersweet experience of crushing hard on someone who didn’t share those feelings. It’s a hundred times worse if you’re their confidant! On the silver screen, you often relate to the wallflower looking onto the dancefloor or the spinster with a knack for romantic poetry, but IRL you’re just as likely to be the party girl whose brazen persona hides romantic disappointment. Nodding to period dramas as well as indie rom-coms, this outfit pairs a whimsical pinafore dress with dramatic faux furs. If you’re going to pine for someone, at least do so in cutting-edge style!


MISHI CLUB – Velvet Puff Sleeve Mini Dress | JY Shoes – Faux Pearl Chunky-Heel Loafers
romand – Han All Fix Mascara | 3CE – Soft Lip Lacquer

Heartbreak can be emotional hell, but there’s something compelling about watching doomed romances on screen, especially when the heroines of ill-fated romances always have the most sumptuous outfits. Just look at Juliet’s iconic white gown in the 1996 Shakespeare adaptation Romeo + Juliet , or Satine’s red dress in the 2001 musical Moulin Rouge! Inspired by the intensity of these stories, I opted for a gothcore ensemble that’s simple yet dramatic. Anchored by a velvet mini dress with puff sleeves and chunky loafers embellished with faux pearls and gold metal details, this is a date outfit for those who tend to fall hard and fast when it comes to matters of the heart. For optimal impact, go bold with spider lashes and red lips. If you must use bling, stick to discreet hoop earrings.


LIVA GIRL – Cutout Crop Top | GUMZZI – Pleated Mini Skirt | SouthBay Shoes – White Sneakers
Hat Society – Tie Dye Baseball Cap | Yukami – Hair Claw | Isle of Green – Twisted Hoop Earrings

Passionate yet short-lived, the summer fling at a picturesque location is a movie genre staple, whether the protagonist is on a Paris-bound train or a fictional Greek island. There’s just something about warm, balmy weather that provides the perfect backdrop for a romantic encounter! Inspired by classic athletic gear and Y2K fashion trends, I created an outfit that Regina George of Mean Girls would play tennis in. Not only is this crop top and pleated skirt combo great for showing off sun-kissed skin, it’s just the right balance between sweet and naughty. Summer is still a long way off, but it’s never too early to file away style inspo for future romantic opportunities! Your week-long fling could very well lead onto bigger things. If not, you’ll always have the memories.


MISHI CLUB – Frill Trim Heart Patch Denim Shacket | MISHI CLUB – Bootcut Jeans
LIPHOP – Zipped Shoulder Bag
| Megan – Block Heel Buckled Slingbacks | Miss Daily – Velvet Headband

Whirlwind romances usually have a short life span, but some do end happily ever after in the form of a steady relationship or domestic bliss. Here’s a sartorial ode to that love you never expected to last, but continues to go strong despite the odds. Instead of a floral mini dress, sexy slip dress or vintage-style midi skirt, I went for a sleek take on 90s grunge that combines street style energy with lady-like touches. Anchored by a comfy denim shacket embellished with heart-shaped appliques and bootcut black jeans, this outfit juxtaposes femme details with edgy vibes. For pops of color, I added ivory slingbacks and a velvet headband. Sweet yet edgy, this low-key take on the date outfit shows that true happiness doesn’t require flashy style.


SugaYuja – Long Sleeve Cargo Jumpsuit | romand – Better Than Eyes Hanbok Project
Diamante – Gradient Croc Grain Crossbody Bag
| Shanhoo – Faux Leather Platform Sneakers

This toxic romance with a sexy significant other who is fundamentally incompatible with you is always in danger of combusting – but you just can’t bring yourself to say goodbye yet. In the process, you’ve become an expert in the art of seduction and making dramatic exits. Perfect for rekindling things after an epic split, this purple cargo jumpsuit pulls out all the stops without looking like you’ve tried too hard. To hit that sweet spot between glammed-up and relaxed, sling on this boxy crossbody bag with a faux pearl handle, but keep things casual with chunky sneakers. Finish the look with a smudge of plum eye shadow for a decadent touch, and leave the jumpsuit partially unzipped if you’re feeling bold.


chuu – Cable-Knit Crop Sweater | Tikka High – Tie-Dye Wide Leg Jeans | KATENKELLY – Smiley Hook EarringOlsin – Set: Floral Print Ceramic Drinking Cup + Saucer | Bolitin – Platform Lace Up Shoes

Sometimes, it’s worth being on your own for while after a relationship breakup. Being single can be fabulously fun, especially if you’re an introvert who prefers crocheting sessions to fancy dinner dates. Not only are you free to pursue your hobbies any time of the day, you can also go for the most outré ensembles without judgement from your other half! Looking for lessons on self-care? Whatever your status, channel your inner singleton in the best of ways. Whether it’s organizing a Galentine’s Day hangout or showering yourself with compliments when self-doubt hits, always prioritize your own needs. As for outfits, own your look by experimenting with bold colors, comfy fits and avant garde styles – in short, everything that’s not date-appropriate.

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