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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
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.
AREA Crystal-Straps Mini Dress
Ten Wilde Butterfly Necklace
SteveMadden Lilah Black Heels
StellarWonders Lover's Eye Inspired Custom Hand-painted Ring
Sex and the City
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.
LYS Beauty Speak Love Glossy Lip Treatment Oil
Palmella Pump in Glass
COMMANDO Stretch thong
To All the Boys: P.S. I Still Love You
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.
No Nonsense Opaque Sheer Tights
Simone Rocha Faux Pearl-Embellished Hair Slide
NARS Velvet Matte Lipstick Pencil
Clueless
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.”
Alice + Olivia Harmony Mini Slip Dress
ORGANZA BOYFRIEND SHIRT WHITE
Mali + Lili Faux Fur Strap Baguette Bag
10 Things I Hate About You
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.
GLDN Bessie Hoops
Insecure
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.
CULT GAIA Serita cutout cotton-blend maxi dress
Patala Diamond Ring
Supergoop! Glow Stick Sunscreen SPF 50 PA++++
Crazy Rich Asians
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.
HERMES Twilly d'Hermes Eau de Parfum
Banana Republic Textured Brass Cuff Bracelet
The Holiday
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.
Maje Double-Face Wool Fur-Trim Coat
Madewell High-Rise Skinny Jeans in Danny Wash
GOODEE x Ezcaray Matisse Stripe Mohair & Wool Scarf
Manolo Blahnik Pita Tall Suede Boots
Pretty Woman
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.
Twilight Dress
Pearl Threaders
Wallaroo Hat Company Women’s Julia Sun Hat
Sex Education
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.
Diorshow On Stage Liquid Eyeliner
MANGO Printed shirt dress
J.Crew Colorful floral hoop earrings
Madison is a senior writer/editor at ELLE.com, covering news, politics, and culture. When she's not on the internet, you can most likely find her taking a nap or eating banana bread.
