The Best '90s Movie Outfits That Are Still Trending In 2020

by Danielle Naer

1990s fashion continues to capture cultural interest, even almost 30 years down the line. In fact, the fitted cardigans, high-rise jeans, and oversized button-downs you wore in school photos are cool all over again. But, beyond your own closet, there are plenty of inspired films from the time to look to for trend inspiration. The best '90s movies outfits are worth revisiting in 2020, and they're much easier to style than you'd think. Kicking off a retrospective of the decade with Vivian Ward's style evolution in Pretty Woman, and leading into the pristine looks of Elizabeth James in The Parent Trap, there's tons to sort through — and emulate — within the ten-year span.

Favorite '90s starlets include Cameron Diaz, who spellbound audiences with her performance in There's Something About Mary; Sharon Stone, who's 30 outfit changes in Casino made the film a favorite amongst the style set. And, of course, Alicia Silverstone's Cher in Clueless, who convinced the masses that a yellow plaid ensemble was worthy of a spot every closet. And wether you'd rather re-watch an outlaw adventure (Thelma & Louise) or a beauty pageant turned dangerous (Miss Congeniality) in the round-up ahead, you'll find 15 films to add to your queue for nostalgic style inspiration.

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There's Something About Mary (1998)

Cameron Diaz's classic cardigan is a big screen that fans can easily re-work into their wardrobe today.

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Never Been Kissed (1999)

Long before Anna Wintour would wear ostrich feathers to the Met Gala, Drew Barrymore did it the back-to-school way in Never Been Kissed.

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Pretty Woman (1990)

Julia Roberts became the biggest style crush of the '90s thanks to the iconic scenes of Pretty Woman. While her red evening dress and white cut-out dress have become iconic silhouettes associated with the film, her oversized button-down is the epitome of early '90s style.

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Casino (1995)

Sharon Stone's Ginger in Casino is the ideal alter-ego — half because of her no-nonsense attitude, and half because of her exorbitant style. Her vintage beaded dress infuses '70s textures with '90s glamour seamlessly.

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Parent Trap (1998)

A white trench moment never fails, and mom Elizabeth James' tonally-synced look is proof. As a wedding gown designer, it's no surprise that she nails off-white.

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Always (1989)

At the crest of the new decade (and as Audrey Hepburn's final film in her glittering career), Always is well worth mentioning. Here, Hepburn reminds us of the impetus of summer whites, wearing a cable-knit tunic and linen pants for much of the film.

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Clueless (1995)

At Beverly Hills High, plaid was in constant rotation, thanks to Alicia Silverstone's Cher and friends. Gucci's marigold skirt shares the same geometric language, and it's just as chic in 2020.

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American Beauty (1999)

In the dark drama American Beauty, Mena Suvari received accolades for her performance. Her youthful style can still be drawn from today — and her down vest is the perfect place to start.

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Love Field (1992)

Michelle Pfeiffer became the '80s It-girl after appearing in Scarface, and her platinum blonde hair and colorful suiting in Love Field is worthy of a revisit today. Her brocade blazer is still super chic, and you can find a similar style in cornflower blue from Rosie Assoulin.

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Freeway (1996)

Before she was Elle Woods, Reese Witherspoon co-starred alongside Brooke Shields and Kiefer Sutherland in this thriller. Electric orange is a recurring hue throughout the entire film, but Wood's miniskirt is an easy place to start.

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One Fine Day (1996)

Michelle Pfeiffer's relaxed trench was the unisex staple of the late '80s and early '90s and tailored iterations have made a strong return in the last few seasons. Burberry's maintains the quintessence of the time, with a few structural updates that keep it contemporary.

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Great Expectations (1998)

Ahead of her Oscar-winning performance in Shakespeare in Love, Paltrow starred in the on-screen adaptation of Charles Dickens' Great Expectations. Her single-buttoning shamrock-green cardigan and skirt set have made a huge comeback in 2020, where knit matching sets are frequent players in the loungewear space.

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Great Expectations (1998)

Thelma & Louise (1991)

For a look that's a bit more rough around the edges, try a cutoff biker tee, like those donned in Thelma & Louise. Saint Laurent makes several iterations that have just the right amount of edge.

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First Wive's Club (1996)

This comedy starring Diane Keaton, Bette Midler, and Goldie Hawn will convince you that a white blazer is a wardrobe must.


First Wive's Club (1996)

Miss Congeniality (2000)

Bullock's trilogy is replete with polished looks, but her baby pink strapless dress is undoubtably one of the best.

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