The Most Stylish Movie Pajama Moments From the '90s and '00s
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When I'm not getting dressed in order to improve my mood during this social distancing, I'm in PJs — what else? Part of my fashion research during this downtime has been to test the waters when it comes to channeling my inner boudoir queen, this being a trend we're going to see on the streets once we go back outside, anyway. Silk slips, dreamy prairie dresses and tops, and slipper-inspired mules are all high on my spring 2020 shopping list right now, and I don't think it's just because I'm sleepy. I'm sure the designers who sent romantic loungewear down their runways would agree.
Of course, I take influence from some of the best films with stylish sleepover moments, too, and I traced these as far back as the late 1970s — I couldn't leave out Rizzo's iconic "Sandra Dee" moment in Grease — late '90s, and early 2000s. From oversize menswear to silk slips and sleep masks (Jenna Rink did the combination best with a trench coat and heels, bringing a whole new meaning to the phrase "I woke up like this"), I'm counting down the best pajama moments from the big screen. Scroll through to see my favorite scenes, and let me know if I missed any other looks that'd be great to re-create right about now.
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Rizzo in Grease, 1978
Rizzo makes fun of "Sandra Dee" at the Pink Ladies pajama party in a lavender oversize button-down, sleeves rolled up to the perfect spot. I always loved this sexy, menswear-inspired look.
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ASOS Design Rolled Up Short Sleeve Shirt
ASOS Design Rolled Up Short Sleeve Shirt ($29, originally $45)
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Jenna Rink in 13 Going on 30, 2004
Jennifer Garner pulled off this lingerie slip so well with the groovy multicolor sleep mask that she later wears onto the street and straight into the office with a trench coat and heeled sandals.
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Only Hearts Silk Charmeuse Mini Slip Dress
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Rosemary in Shallow Hal, 2001
Gwyneth Paltrow nailed this ultrasexy moment in a sheer ruffled minidress, a lingerie set, and pumps before she got into bed with Hal.
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For Love & Lemons Harper Ruffle Slip Dress in Periwinkle
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Lux Lisbon in The Virgin Suicides, 1999
Kirsten Dunst set the tone in romantic prairie-girl nightgowns in Sofia Coppola's The Virgin Suicides.
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Sleeper Atlanta Linen Dress in Linum Print
Sleeper Atlanta Linen Dress in Linum Print ($224, originally $320)
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Carrie Bradshaw in Sex and the City: The Movie, 2008
I will never forget how Sarah Jessica Parker wore a purple silk tank and one long strand of pearls as she read Love Letters of Great Men to Big in bed. "Ever thine, ever mine, ever ours."
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Shein Contrast Lace Satin Slips
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BaubleBar Long Freshwater & Imitation Pearl Necklace
BaubleBar Long Freshwater & Imitation Pearl Necklace ($26, originally $44)
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Susanna in Girl, Interrupted, 1999
Winona Ryder looked so effortless with nothing but a guitar in wool floral-print pajamas. She definitely makes a loungewear set look cooler than most — and she's sitting next to Angelina Jolie, mind you.
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Loft Floral Pajama Set
Loft Plus Floral Pajama Top ($35) and Loft Plus Floral Pajama Pants ($40)
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Lucy in Crossroads, 2002
Britney Spears takes me back to my Limited Too days, when I used to watch Crossroads on repeat. The only thing that's missing from her butterfly PJ pants and tiny little camisole look is a pair of butterfly clips for her crimped hair.
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Sleepy Wilson Poppy Silk Pyjama Trousers in Rainforest
Sleepy Wilson Poppy Silk Pyjama Trousers in Rainforest ($144, originally $205)
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