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Fashion

Winona Ryder's Style Evolution, From '90s Cool To Haute Couture

by Erika Harwood

Winona Ryder is a Hollywood legend. The actor has been a red carpet fixture since the 1980s, wearing everything from trench coat dresses to flip flops to Dior couture. See Ryder's decades-long style evolution ahead.

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1989, Oscars

Wearing a black dress and tights to the 1989 Oscars with Heathers co-star Christian Slater.

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1990, Edward Scissorhands premiere

Wearing a trench coat mini-dress to the 1990 premiere of Edward Scissorhands with Johnny Depp.

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1992, Dracula premiere

Wearing a blue pleated skirt suit to the 1992 premiere of Dracula.

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1994, Oscars

Wearing a sequined fringe gown to the 1994 Oscars.

Ron Galella/Ron Galella Collection/Getty Images
1996, Vanity Fair Oscar Party

Wearing a blush gown and matching shawl to the 1996 Vanity Fair Oscar Party.

Jim Smeal/Ron Galella Collection/Getty Images
1997, AFI Tribute to Martin Scorsese

Wearing a fitted red dress to the AFI Tribute to Martin Scorsese in 1997.

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1998, MTV VMAs

Keeping it '90s casual in black flip flops and a sweater tied around her waist to the 1998 VMAs.

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2000, Golden Globes

Wearing a white gown to the 2000 Golden Globes with Matt Damon.

Photo by Sylvain Gaboury/FilmMagic
2004, The American Museum of the Moving Image Honors Richard Gere

Wearing an off-the-shoulder red gown to an American Museum of the Moving Image event for Richard Gere in 2004.

Photo by Ryan Born/WireImage
2007, Met Gala

Wearing a strapless black gown with an oversized bow to the Met Gala in 1997.

Photo by Fotonoticias/WireImage
2008, Marie Claire Prix De La Mode

Wearing a nude dress to the Marie Claire Prix De La Mode.

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2010, Black Swan press conference

Wearing a sweater vest and cardigan to a Black Swan press conference in 2010.

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2010, Black Swan premiere

Wearing a black tuxedo to the premiere of Black Swan in 2010.

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2011, SAG Awards

Wearing a ruffled white gown to the 2011 SAG Awards.

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2012, Frankenweenie premiere

Channeling Wednesday Addams at the 2012 premiere of Frankenweenie.

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2016, Stranger Things premiere

Wearing a black pantsuit and suit jacket to the premiere of Stranger Things in 2016.

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2017, Golden Globes

Wearing a custom Viktor & Rolf strapless black gown to the 2017 SAG Awards.

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2017, Stranger Things season 2 premiere

Wearing a black dress cinched with a bow to the 2017 premiere of Stranger Things season 2.

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2018, SAG Awards

Wearing a black dress and suit jacket to the 2018 SAG Awards.

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2019, Stranger Things photocall

Wearing black jeans and a Tilda Swinton T-shirt to a photocall for Stranger Things in 2019.

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2020, SAG Awards

Wearing Dior couture to the 2020 SAG Awards.

See more Hollywood style evolutions from Amandla Stenberg, Lily Collins, and Zoe Kravitz.

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