Leon Bennett/Getty Images Entertainment/Getty Images

Fashion

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

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.

Ron Galella/Ron Galella Collection/Getty Images
1989, Oscars

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

Ron Galella/Ron Galella Collection/Getty Images
1990, Edward Scissorhands premiere

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

Ron Galella, Ltd./Ron Galella Collection/Getty Images
1992, Dracula premiere

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

Ron Galella/Ron Galella Collection/Getty Images
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.

Jeff Kravitz/FilmMagic, Inc/Getty Images
1998, MTV VMAs

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

Ron Galella, Ltd./Ron Galella Collection/Getty Images
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.

Jason Merritt/Getty Images Entertainment/Getty Images
2010, Black Swan press conference

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

Michael N. Todaro/FilmMagic/Getty Images
2010, Black Swan premiere

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

Frazer Harrison/Getty Images Entertainment/Getty Images
2011, SAG Awards

Wearing a ruffled white gown to the 2011 SAG Awards.

Rick Kern/WireImage/Getty Images
2012, Frankenweenie premiere

Channeling Wednesday Addams at the 2012 premiere of Frankenweenie.

Jason LaVeris/FilmMagic/Getty Images
2016, Stranger Things premiere

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

Frazer Harrison/Getty Images Entertainment/Getty Images
2017, Golden Globes

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

Frazer Harrison/Getty Images Entertainment/Getty Images
2017, Stranger Things season 2 premiere

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

Alberto E. Rodriguez/Getty Images Entertainment/Getty Images
2018, SAG Awards

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

Jerod Harris/WireImage/Getty Images
2019, Stranger Things photocall

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

Gregg DeGuire/Getty Images Entertainment/Getty Images
2020, SAG Awards

Wearing Dior couture to the 2020 SAG Awards.

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

More from NYLON

Lili Reinhart's Style Evolution, From Simple Dresses To Couture Looks
By Erika Harwood
Zoë Kravitz's Style Evolution, From Cowboy Hats At The Grammys to Couture At The Met Gala
By Erika Harwood
Ariana Grande's Style Evolution, From Nickelodeon Star To Red Carpet Powerhouse
By Erika Harwood
fb
x