8 Outfits to Wear for Valentine's Day, Inspired By Your Favorite Rom-Com Characters

·6 min read
Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

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Whether you're getting together with your girlfriends, wining and dining with your spouse, or observing Valentine's Day solo with some yummy takeout and a night of self-care, dressing for the occasion can make any plan feel a little more special. But if you're blanking on what to wear this year, not to worry. Outfit inspiration is plentiful among our favorite rom-com characters.

Think about it: we're constantly looking to celebrities for outfit ideas, so why not consider the date-night stylings of the fictional personas they portray on screen? Ahead, we've recreated some of our personal favorite looks from romantic comedies, with a mixture of options from classic flicks like Pretty in Pink, to the laugh-out-loud Netflix original, Lovebirds.

RELATED: 10 Stylist-Approved Valentine's Day Outfits For Every Type of Date Night

Lara Jean Covey in To All The Boys I Loved Before P.S. I Still Love You

Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

Netflix

If we were to tier-rank all rom-coms that actually take place on or around Valentine's Day, To All The Boys I Loved Before, P.S. I Still Love You would easily make top three. This is partially because Lara Jean Covey (played by Lana Condor) and Peter Kavinsky (Noah Centineo) have enough chemistry to set a lab on fire, and partially because Lara Jean dresses perfectly for the occasion. And while, sure, heart prints can be kind of cheesy and overdone, Lara Jean's A-line dress with red hearts swirling around the white fabric is a tasteful, stylish way to don the trend.

Shop Similar: Cider Heart Print Bowknot Midi Dress ($32); Gorjana Bespoke Wilder Heart Necklace ($85)

Leilani in Lovebirds

Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

Netflix

If you and your significant other are more com than rom, Leilani's (Issa Rae) playful and hilarious unicorn ensemble in Love Birds will undoubtedly have your date's full attention. Complete with hot pink metallic pants and a rainbow unicorn horned hoodie, this mythical fit is colorful, unique, and super comfortable — an ideal combination for an evening vegging out on the couch.

Shop Similar: Yanekop Womens Sherpa Pullover, ($30); Athleta Salutation Stash Pocket II 7/8 Tight ($98)

RELATED: Issa Rae's Wedding Day Ponytail Almost Goes Down to Her Butt

Annie Reed in Sleepless in Seattle

Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

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Annie Reed (Meg Ryan) is the queen of layering and practical dressing. From her first to last outfit in Sleepless in Seattle, the hopeless romantic was always appropriately dressed, no matter the occasion. We especially love her Valentine's Day uniform, which included a simple, black crewneck dress for her breakup dinner with Walter, as well as the slate grey coat and floral scarf that she threw on to trek across a very fridgid-looking NYC to the Empire State Building. She's wearing this iconic look when she comes face-to-face with Sam Baldwin (a very hunky Tom Hanks), so if you're trying to channel some movie-like love story energy, this may be the fit for you.

Shop Similar: Eileen Fisher Stretch Jersey Knit Crew Neck Dress ($198); Universal Standard Derjon Trench Coat ($188); Lafayette 148 New York Medium Nova Scarf ($298); Sheertex Essential Sheer Tights ($29)

Laney Boggs in She's All That

Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

Alamy

The best part about Laney Boggs's makeover moment in She's All That is when she comes down the stairs in slow-mo. Six Pence None the Richer's Kiss Me is blasting in the background and just as Boggs (Rachel Leigh Cook) locks eyes with Zack Siler (Freddie Prinze Jr.), she trips into his arms because she's not used to walking in chunky platforms. Relatable. The second best part of this scene, however, is the sexy red mini dress Siler's sister picks out for this 'nerd-turned-hottie,' along with her black micro purse, which, evidently, Sarah Jessica Parker's trying to make happen again for 2022.

Shop Similar: Urban Outfitters UO Mallory Cowl Neck Slip Dress ($49); Journee Collection Nairr Platform Sandal ($60); Zara Mini City Bag ($36)

RELATED: Addison Rae Loved the Laney's Overall Outfit from She's All That

Jenna Rink in 13 Going on 30

Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

Getty Images

There are so many iconic outfits worn by Jenna Rink (Jennifer Garner) in 13 Going on 30, from the multicolor cutout Versace dress (check out an affordable dupe from Cider) to her lingerie-and-blazer pairing from the start of her (temporary) adulthood. But for a Valentine's date, this floral dress with a sweetheart neckline (you know, the one she wears with a pink ribbon in her hair) feels like a cute and fairly easy choice. Just don't forget your pearls.

Shop Similar: Selkie La Belle Etoile Cottage Puff Dress ($295); Lulus Junia Light Nude Patent Ankle Strap Pumps, Montserrat Las Tres Perlas Choker ($110)

Bridget Jones in Bridget Jones's Diary

Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

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Bridget Jones (Renée Zellweger) kicks off the franchise in a pair of red pajamas printed with penguins and snowflakes, belting the lyrics to Jamie O'Neal's rendition of All By Myself into her glass of wine. To be clear, spending Valentine's Day alone doesn't have to be sad, especially if you turn it into a spa night for one. So take a page from Bridget's book and slip into a pair of festive pjs, pair them with your fuzziest socks, pour yourself a glass of wine, and enjoy a night entirely on your terms.

Shop Similar: Intimissimi Long-Sleeve Micromodal Pajama Top ($48, Originally $59); Intimissimi Long Micromodal Trousers ($32, Originally $39); UGG Cozy Chenille Socks ($20)

RELATED: Jennifer Garner Just Wore Lake Pajamas, and Shoppers Say They Are "Perfect"

Charlie Cantilini in Monster-in-Law

Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

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Jennifer Lopez actually has a lot in common with her rom-com alter ego Charlie Cantilini. Both women are unapologetically themselves in every aspect of life — especially when it comes to their wardrobes. Charlie even wears a poncho while having lunch with her future mother-in-law Viola (played by the fabulous Jane Fonda), and in 2022, the style has seemingly returned, backed by Lopez herself. However, if the choice of a bright-on-bright color combination feels too far outside your comfort zone, you can easily trade one of these pieces for a neutral alternative. But just FYI, yellow is going to be huge this spring, and crochet everything has been having a moment since early 2021, so following this leading lady's choices might be a good idea, even beyond February 14.

Shop Similar: Urban Renewal Vintage Patterned Cape ($39); Rhode Celeste Knit Scoop Neck Dress ($375); The Hair Edit Gold Loop Claw Clip ($10)

Andie Walsh in Pretty in Pink

Valentine’s Day Outfits Based On Your Favorite Rom Coms
Valentine’s Day Outfits Based On Your Favorite Rom Coms

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It doesn't get much better than Molly Ringwald as quirky creative Andie Walsh, who is simply trying to survive high school in Pretty in Pink. When preppy heartthrob Blane McDonough (Andrew McCarthy) leaves her dateless for senior prom, Andie designs the best revenge dress in '80s cinema, and goes to the dance solo looking absolutely amazing. Lucky for us, '80s fashion is making a cameo in 2022, so no amount of volume, lace, polkadots, and cold shoulder cutouts is too much.

Shop Similar: Aje Casabianca Braided Asymmetric Puff Sleeve Mini Dress ($455)