It’s been nearly two years of pandemic evenings spent inside binge-watching every TV show and movie available via streaming. Now, as we start to consider dressing for Valentine’s Day, it feels only natural to draw inspiration from the same people we’ve shared so many late nights with. Here, just 10 of the on-screen date looks we’ll never forget, plus how to pull them off IRL.
My Date With the President’s Daughter
United Archives GmbH / Alamy Stock Photo
If you’re a ’90s kid, you’ve been thinking about emulating Hallie Richmond’s thrift store outfit for decades, blinking eye ring and all. This is your sign to finally go for it.
Sex and the City
HBO
Put your mixed feelings about And Just Like That… aside, and focus on what we can all agree on: Carrie Bradshaw’s naked dress is still a knockout.
To All the Boys: P.S. I Still Love You
Netflix
After an entire movie of wondering will-they-won’t-they, viewers finally get to see Lara Jean and Peter’s first real date in the To All the Boys sequel. Lara Jean goes rom-com classic with a bow-adorned red dress and matching lip, making her the perfect inspiration for those who like to approach Valentine’s Day a bit more literally.
Clueless
CBS Photo ArchiveGetty Images
You might not be able to get the Calvin Klein version of this classic Clueless dress, but somehow I still think Cher Horowitz would approve of anyone trying to channel her all-white date night look. But you are legally obligated to throw on a sheer button-up as your “jacket.”
10 Things I Hate About You
Courtesy Everett Collection
If your Valentine’s Day plans fall more along the lines of ditching detention, playing paintball, and going on a paddle boat ride, then consider Kat Stratford’s casual-yet-somehow-still-festive ’fit.
Insecure
HBO
I’d offer you Molly Carter’s entire Insecure wardrobe if I could, but for a Valentine’s Day spent in a tropical locale, I must insist you channel this cut-out Cult Gaia look.
Crazy Rich Asians
Sanja Bucko
Sure, Rachel wore this Missoni number to meet the Young family (aka not totally a date), but her rainbow dress and gold accessories are the perfect antidote to this endless pandemic winter.
The Holiday
©Columbia Pictures/Courtesy Everett Collection
The only thing better than being a main character is being a main character in a Nancy Meyers movie. Plus, thankfully, The Holiday’s quaint English setting gives way to a number of seasonally-appropriate looks.
Pretty Woman
Hulton Archive
Your new plan for Feb. 14: Show up in a polka dot dress with matching accessories and ask your partner to take you on a giant shopping spree, Pretty Woman-style.
Sex Education
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Despite these characters’ current relationship statuses, the Eric-Adam-Otis-Ruby double date is still the greatest of all time. Sartorially, feel free to choose your fighter: Eric’s green glitter ensemble paired with bright blue eyeliner or Ruby’s colorful patterned dress with coordinating earrings.
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