'90s-Inspired Outfits For Your Next Holiday Party

Channel your inner Winona for the night.

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Winona Ryder white dress

The internet is in no short supply of soliloquies waxing poetic about the ‘90s — but that’s for good reason. It was a decade of fashion industry firsts (ahem, supermodels) and of boundary-pushing style, from Calvin Klein minimalism all the way to grunge and hip-hop fashion. Tied to the trends was a party scene that warranted a new era of slinky, celebratory dressing. Now, with December in full swing, why not take a gander at ‘90s-inspired holiday party outfits to inform your evenings out for the month ahead?

On the 1990s soirée circuit were the women who would go on to become synonymous with this era’s most defining trends, such as Kate Moss, Naomi Campbell, and Winona Ryder. And while there were the iconic pieces like slip dresses and chokers, other going-out staples were also in the mix during this period of time — and conveniently translate to a modern context. Helping to prove this point, the 10 looks below from style icons of the ‘90s all feature silhouettes, fabrics, and details that are worthy of imitating for your next evening out during the holiday party season. Take a walk down memory lane and snag a new piece for the weekend.

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Kate Moss’ Feathers

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Kicking things off with the queen of effortlessly cool ‘90s style, Kate Moss illustrates the timelessness of a feather-embellished frock. Not only is this texture ideal for swaying about a dance floor, it also photographs beautifully.

Heather Graham’s Leather

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A little bit Matrix, a little bit sensual — the allover leather (or vegan leather) dress feels fresh for a holiday party when done simply, as Heather Graham proves in her edgy look above. Complement the outfit with simple hair and makeup to let the dress take the spotlight.

Winona Ryder’s Fringe

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You need little explanation for why a fringe dress is festive, but Winona Ryder is a solid reminder that this embellishment reigns supreme when it comes to holiday parties.

Aaliyah’s Thigh Slit

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Sometimes a flash of skin can feel like just the right amount of festive for a holiday party look, even if you’re wearing a simple neutral dress, like Aaliyah. Whether you go minimalist or maximalist, a little leg is never a bad idea.

Halle Berry’s Velvet

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Velvet is the unofficial fabric of the holidays. Halle Berry’s deep blue dress crafted in this luxurious texture looks especially chic thanks to the long sleeves and open back detail.

Drew Barrymore’s Choker

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No ‘90s roundup is complete without a choker reference, and Drew Barrymore’s pearl version is especially cool for the moment. Follow her lead and pair yours with a simple sleeveless LBD. Might as well wear the brown lipstick while you’re at it.

Jennifer Aniston’s Bare Midriff

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Sometimes, finding a slightly new or unique way to bare your midriff (à la Jennifer Aniston) is the easiest way to reinvigorate your party wardrobe. Whether it’s a floor-length, open-front tunic or a blouse with an interesting front detail, finding a special piece like this will be an investment worth holding onto.

Princess Diana’s Statement Straps

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As you can see, the key to a signature party piece is all in the details, which is why Princess Diana’s chain link-strap dress is appealing. Beading, a bow, or something in between, a spaghetti strap dress that gives something extra will pay off.

Naomi Campbell’s Check Print

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Cozy weather calls for check prints, which is why Naomi Campbell’s printed set serves as the ultimate style inspo. Take a page from her book and wear head-to-toe pattern or simply add a separate to your outfit for a subtler take on the plaid trend.

Kate Moss’ Slip Dress

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Because one Kate Moss look is never enough, the ultimate 1990s style staple: the slip dress. Wear it with your favorite pair of strappy sandals and reap the benefits of an effortless, elegant holiday party ensemble.