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New Year's Eve Outfit Ideas Inspired By Your Favorite '90s Rom-Coms

They’re anything but overrated.

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It’s that weird time in between Christmas and the New Year where I don’t remember what day it is and I have absolutely nothing to do. I’m not complaining — I love days that are filled with hot beverages, sweats, and bingeing ‘90s rom-coms. I know we keep talking about that era and how influential it was (and still is), particularly for fashion, but there is no denying that the ‘90s will continue to grip 2023.

I realized that while looking more closely at Julia Roberts’ outfits in the 1999 cinematic hit, Notting Hill. The movie star offered something more than just entertainment. Her character Anna Scott wore outfits that I actually want to wear right now. In her opening scene she wears a black Chanel beret, cat eye sunglasses, pinstripe trousers, and an oversized leather bike jacket. It’s as if she jumped right out of my Instagram saved folder.

Since I could not figure out my New Years Eve look this year, I challenged myself to rewatch my favorite movies to see if I could find party inspiration in each of them. What I discovered in revisiting these films was unexpected, and let’s just say, I know New Years Eve can be overrated, but follow my advice and your outfit definitely won’t be. From Dionne Davenport to Josie Geller, ahead are eight last-minute NYE party looks inspired by your favorite on-screen ‘90s heroines.

Clueless, 1995

Paramount Pictures

First up, we have none other than the boundary pushing Dionne from Clueless. “I must give her props for her courageous fashion efforts,” says Cher Horowitz about her best friend in the opening scene of the movie. Mini skirts are all the rage right now — even in colder weather. Pair with knee-high patent leather boots, a turtleneck, and cropped blazer to complete the look.

Romy & Michele’s High School Reunion, 1997

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Leave it to best friends Romy and Michele to teach you a thing or two about pretending to be successful this New Year’s Eve with their unmistakable baby pink and blue minidresses. Add a fun pair of shoes to start this year on a playful note.

How Stella Got Her Groove Back, 1998

20th Century Fox

Angela Bassett showed us how to nail a laced party look in this 1998 cult classic while dancing the night away as a successful corporate executive looking for love. I don’t think it was any coincidence that she wore lace in this scene since historically it was considered a symbolic textile of the wealthy and powerful. Lace can also be considered romantic which is why I think it is ideal to wear on New Years Eve.

Can’t Hardly Wait, 1998

Columbia Tristar/Kobal/Shutterstock

For all you single ladies, please take note of how Amanda Beckett kept it minimal for her single-girl era with her baby blue tank top and navy midi skirt. Sometimes simple looks make the greatest outfits.

She’s All That, 1999


Every time I see this image, “Kiss Me” by Sixpence None The Richer starts playing in my head. This epic walk (and subsequent fall) down the stairs is one of the most iconic transformation reveals in ‘90s rom-com history. Lainey Boggs’ red minidress with the sweetheart neckline and little black purse is what you should be wearing in hopes of finding your own Freddie Prince Jr.

Notting Hill, 1999

Universal Pictures

Even though Anna Scott is kind of a morally defunct character as she fails to disclose that she was already in a committed relationship, her outfits are just too good to ignore. My favorite is the look comprised of a sequin black midi skirt, black crop top, oversized biker jacket and old school classic Vans that she changes into after Hugh Grant spills juice all over her. This one has an effortless, cool-girl ring to it.

10 Things I Hate About You, 1999

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I’m so glad Bianca Stratford’s dad finally allowed her to date because her pink tulle moment opposite Joseph Gordon-Levitt is a foolproof way to add color and some texture to winter going-out clothes. I wouldn’t take this prom moment too literally...below is a modern way to recreate it.

Never Been Kissed, 1999

Getty Images/Hulton Archive/Getty Images

It’s hard to believe that Josie Geller wasn’t instantly the most popular girl in school in this white feather boa outfit. Though it may have taken some time to resonate, her outfit is one that I would replicate this New Year’s Eve in a heartbeat.