Winona Ryder’s 12 Best ’90s Outfits (That Look Just as Modern Today)

Leah Bourne

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If the 1990s had crowned an “it” girl, it certainly would’ve been Winona Ryder—she starred in the decade’s ultimate coming of age drama “Reality Bites”, had Johnny Depp on her arm, and spent the better part of her glory years in outfits that set the standard for fashion lovers everywhere.

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If you revisit what Ryder wore during the ’90s, you’ll see her outfits pretty much still rule. Whether she was in a minimalist little black dress and strappy sandals, a leather pencil skirt and tucked-in mock turtleneck, or a beaded cocktail dress, Ryder’s fashion choices look just as modern today as they did twenty years ago. Really now—how many people are able to say that?

MORE: How Uma Thurman’s 1995 Oscar Dress Changed the Red Carpet Forever

Given that designers from Alexander Wang to Rag & Bone are jumping onto the 1990s train in a big way right now, there is no better time to source Ryder’s heyday for outfit ideas. Here, a look at her 12 best outfits from the decade that you need to copy immediately.

Johnny Depp And Winona Ryder

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1. Winona Ryder in a little black dress and ladylike heels.

Ryder wore this ladylike black dress, classic black pumps, and Chanel bag out one night with then-boyfriend Johnny Depp, finishing off her outfit with the perfect red lip. Can we say fashion perfection here, or what?

51st Cannes Film Festival

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2. Winona Ryder in the perfect beaded cocktail dress. 

Swoon-worthy beaded cocktail dress? Check. Wrap necklace? Check. Satin Manolo Blahniks? Check. Can we have this outfit, like now?

"Alien Resurrection" Los Angeles Premiere

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3. Winona Ryder in a black pencil skirt and mock short-sleeved turtleneck.

In an outfit that looks like it could have been ripped from a modern runway, Ryder’s black leather pencil skirt, short-sleeved mock turtleneck, and mule sandals is as flawless as it gets.

U2 "Pop Mart" Tour - Backstage - May 31, 1997

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4. Winona Ryder in a crop top and long pants.

In a look that screams ’90s (in the best possible way), Ryder’s wide-leg black pants and matching crop top, leopard cardigan and delicate necklaces in varying lengths wouldn’t look out of place on a site like Nasty Gal today. FYI, Winona wore this ensemble to a U2 concert in 1997.

American Movie Classics Presents "Ladies of The Musicals"

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5. Winona Ryder in matching dress and shoes. 

Matching your outfit to your shoes is fully back in style, and Winona pulled it off before any of us.

"The Talented Mr. Ripley" Los Angeles Premiere

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6. Winona Ryder in a va-va-voom black dress and fishnet cardigan. 

Notice a theme here? Ryder loved little black dresses and cardigan sweaters in the 1990s. We don’t blame her.

55th Annual Golden Globe Awards

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7. Winona Ryder in a pencil skirt and cardigan.

Steal this styling trick from Ryder, stat: Pair a basic pencil skirt with a buttoned-up cardigan (with no shirt underneath).

Joan of Arc Premiere

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8. Winona Ryder in a statement fur coat. 

We love Ryder’s choice of a statement coat here, combined with a basic black dress and a mini vintage bag.

American Movie Classics 5th Anniversary Film Preservation Festival

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9. Winona Ryder in a 1950s-inspired lace dress. 

Way ahead of her fashion time in this regard, Ryder was a huge fan of vintage and vintage-inspired pieces during the 1990s. This lace 1950s-inspired dress hits all the right notes.

"The Crucible" Los Angeles Premiere

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10. Winona Ryder in an ankle-grazing dress and statement coat. 

We’re seeing ankle-grazing dresses coming back into fashion in a big way. Ryder pulled it off here, topping her black dress with a statement coat.

66th Annual Academy Awards

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11. Winona Ryder in the perfect fringed dress.

Ryder wore this perfect beaded flapper-style fringed dress to the Academy Awards in 1994. One of next season’s biggest trends from New York Fashion Week? Fringe.

"Edward Scissorhands" Premiere

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12. Winona Ryder in a satin shirt-dress. 

Lingerie-inspired looks are everywhere right now. Want to know how to pull it off? Take inspiration from this outfit that Ryder wore way back in 1990—a black flirty satin pajama skirt, black pantyhose, and basic black pumps.