The Winona Ryder Look Book
Photo: Ron Galella, Ltd./WireImage
When Heathers hit theaters in 1988, Winona Ryder was just 17. Like her character Veronica, Ryder’s eighties wardrobe consisted of many oversize blazers and menswear-inspired pieces. As Ryder grew up, starred in Edward Scissorhands, and started dating Johnny Depp, her style evolved — and she began adding leather jackets, cropped pants, and more figure-revealing dresses to her wardrobe. Since then, the actress has adopted and abandoned a bold pixie cut, dabbled in headbands, and paved the way for future troublesome starlets with some memorable outfits for court appearances. In honor of the cult classic Heathers being reinvented as an off-Broadway musical, take a look back at the star’s best fashion moments.
July 11, 2016 Where: At the premiere of 'Stranger Things' in Los Angeles. Photo: Jason LaVeris/FilmMagic
August 11, 2015 Where: At the Show Me A Hero New York screening. Photo: Andrew H. Walker/Getty Images
November 18, 2013 Where: At the Homefront press conference in Beverly Hills, California. Photo: Jason LaVeris/2013 Jason LaVeris
April 29, 2013 Where: At The Iceman screening in New York City. Photo: 2013 Henry S. Dziekan III
April 8, 2013 Where: At the Disconnect New York Special Screening. Photo: 2013 Getty Images
August 30, 2012 Where: At The Iceman Premiere during The Venice Film Festival. Photo: 2012 Venturelli
January 30, 2011 Where: At the Screen Actors Guild Awards in Los Angeles, California. Photo: 2011 Jon Kopaloff
November 11, 2010 Where: At the AFI Fest Closing Night Gala Screening Of Black Swan in Hollywood, California. Photo: 2010 Steve Granitz
May 4, 2009 Where: At "The Model as Muse: Embodying Fashion" Costume Institute Gala in New York City.
November 20, 2008 Where: At Marie Claire Prix de la Mode awards in Madrid, Spain.
Photo: 2008 Getty Images
May 7, 2007 Where: With Marc Jacobs at the "Poiret: King of Fashion" Costume Institute Gala in New York City.
March 5, 2006 Where: At the Vanity Fair Oscar Party Hosted by Graydon Carter.
April 20, 2004 Where: At the American Museum of the Moving Image Benefit Salute to Richard Gere in New York City.
December 11, 2002 Where: Leaving Santa Monica County Building after reporting to the probation office. Photo: 2002 Getty Images
November 6, 2002 Where: At the Beverly Hills Courthouse.
June 3, 2002 Where: Arriving at the Beverly Hills Municipal Court for her preliminary hearing on shoplifting charges. Photo: (?) Copyright 2002 ...
June 3, 2002 Where: Arriving at the Beverly Hills Municipal Court for her preliminary hearing on shoplifting charges. Photo: (?) Copyright 2002 by Getty Images
August 14, 2001 Where: At the UK premiere of Planet of the Apes in London, England.
March 25, 2001 Where: At the Academy Awards in Los Angeles.
October 11, 2000 Where: At the Lost Soul Hollywood Premiere.
Photo: 2000 Ron Galella, Ltd.
October 6, 2000 Where: Getting star on Hollywood Walk of Fame.
September 19, 2000 Where: At Kevyn Aucoin's New Book Face Forward Launch Party in New York City. Photo: 2000 Ron Galella, Ltd.
June 3, 2000 Where: With Jimmy Fallon at the MTV Movie Awards.
March 26, 2000 Where: At the Academy Awards.
February 16, 2000 Where: With Brittany Murphy at Step Up Women's Network Presents V-Day Los Angeles Celebrated with the Production of Eve Ensler'...
February 16, 2000 Where: With Brittany Murphy at Step Up Women's Network Presents V-Day Los Angeles Celebrated with the Production of Eve Ensler's "The Vagina Monologues" and After Party.
January 23, 2000 Where: With Kevyn Aucoin at the Golden Globe Awards in Beverly Hills, California. Photo: 2000 Ron Galella, Ltd.
December 12, 1999 Where: At The Talented Mr. Ripley Los Angeles Premiere.
December 8, 1999 Where: At the Girl, Interrupted Hollywood Premiere.
Photo: 1999 Ron Galella, Ltd.
December 6, 1999 Where: With Angelina Jolie in Girl, Interrupted.
October 28, 1998 Where: At the Living Out Loud premiere. Photo: 1998 Ron Galella, Ltd.
September 25, 1998 Where: At the opening of Celebrity in New York City. Photo: 1998/Daily News, L.P. (New York)
September 10, 1998 Where: At the MTV Video Music Awards.
June 23, 1998 Where: At the premiere of Smoke Signals in New York City.
May 21, 1998 Where: At the Cannes Film Festival.
May 21, 1998 Where: At the Cannes Film Festival.
March 23, 1998 Where: At the Vanity Fair Oscar Party.
November 20, 1997 Where: At the Alien: Resurrection premiere. Photo: 1997 Ron Galella, Ltd.
September 25, 1997 Where: At the American Movie Classics' Fifth Annual Film Preservation Festival "Salute to Film Noir" in Los Angeles,...
September 25, 1997 Where: At the American Movie Classics' Fifth Annual Film Preservation Festival "Salute to Film Noir" in Los Angeles, California. Photo: 1997 Ron Galella, Ltd.
July 30, 1997 Where: With Gwyneth Paltrow departing for New York City from the Los Angeles International Airport. Photo: 1997 Ron Galella, Ltd.
May 31, 1997 Where: Backstage at the U2 "Pop Mart" tour.
March 24, 1997 Where: At the Vanity Fair Oscar Party.
February 20, 1997 Where: At the AFI Tribute to Martin Scorsese.
November 20, 1996 Where: At The Crucible premiere in Beverly Hills, California. Photo: 1996 Ron Galella, Ltd.
October 16, 1996 Where: With Claire Danes at premiere of To Gillian On Her 37th Birthday. Date created: 16 Oct 1996
September 12, 1996 Where: With Giorgio Armani at a Giorgio Armani party.
June 12, 1996 Where: At Ladies of The Musicals in Beverly Hills, California.
March 25, 1996 Where: At the Academy Awards.
January 17, 1996 Where: With Claire Danes at the Fire & Ice Ball to Benefit Revlon/UCLA Women's Cancer Research. Photo: 1996 Ron Galella, Lt...
January 17, 1996 Where: With Claire Danes at the Fire & Ice Ball to Benefit Revlon/UCLA Women's Cancer Research. Photo: 1996 Ron Galella, Ltd.
Circa 1996 Where: At the Armani Store opening in New York City.
March 25, 1995 Where: With Dave Pirner at the IFP/West Independent Spirit Awards.
March 1, 1995 Where: With Dave Pirner at the Academy Awards in Los Angeles, California. Photo: 2003 Getty Images
December 11, 1994 Where: With Dave Pirnerat the Little Women premiere. Photo: 1994 Ron Galella, Ltd.
March 21, 1994 Where: At the Academy Awards.
February 16, 1994 Where: With Dave Pirner at the Reality Bites premiere. Photo: 1994 Ron Galella, Ltd.
January 22, 1994 Where: At the Golden Globe Awards in Beverly Hills, California. Photo: 1994 Ron Galella, Ltd.
Circa 1994 Where: With Ethan Hawke in Reality Bites. Photo: 2012 Getty Images
December 8, 1993 Where: With Liz Phair and Rosanna Arquette during Liz Phair and Beck perform at McCabe's Guitar Store in Santa Monica.
September 13, 1993 September 13, 1993 Where: With Dave Pirner at The Age of Innocence premiere in New York City. Photo: 1993 Ron Galella, Ltd.
November 10, 1992 Where: At the Dracula Hollywood Premiere. Photo: 1992 Ron Galella, Ltd.
April 28, 1992 Where: At the Night on Earth New York City Premiere. Photo: 1992 Ron Galella, Ltd.
October 3, 1991 Where: At the Little Man Tate New York City Premiere. Photo: 1991 Ron Galella, Ltd.
September 19, 1991 Where: At the Rambling Rose premiere. Photo: 1991 Ron Galella, Ltd.
August 7, 1991 Where: At The Commitments Hollywood Premiere. Photo: 1991 Ron Galella, Ltd.
May 22, 1991 Where: At the Backdraft Beverly Hills Premiere. Photo: 1991 Ron Galella, Ltd.
May 20, 1991 Where: At the Hudson Hawk Westwood premiere. Photo: 1991 Ron Galella, Ltd.
April 26, 1991 Where: At the Brookly Laundry Play Performance in West Hollywood, California. Photo: 1991 Ron Galella, Ltd.
March 22, 1991 Where: At the American Cinematheque Award Salute to Martin Scorsese in Los Angeles, California. Photo: 1991 Ron Galella, Ltd.
February 1, 1991 Where: With Johnny Depp at The Silence of the Lambs premiere. Photo: 1991 Ron Galella, Ltd.
January 19, 1991 Where: With Johnny Depp at the Golden Globe Awards in Beverly Hills, California. Photo: 1991 Ron Galella, Ltd.
December 10, 1990 Where: With Johnny Depp at the Mermaids Beverly Hills premiere. Photo: 1990 Ron Galella, Ltd.
December 6, 1990 Where: With Johnny Depp at the Edward Scissorhands Premiere. Photo: 1990 Ron Galella, Ltd.
September 24, 1990 Where: With Johnny Depp at the Pacific Heights premiere. Photo: 1990 Ron Galella, Ltd.
September 18, 1990 Where: With Johnny Depp at Herb Ritts' Birthday Party.
July 29, 1990 Where: Arriving at the Los Angeles International Airport. Photo: 1990 Ron Galella, Ltd.
July 1, 1990 Where: With Johnny Depp at the Cry-Baby Premiere.
June 14, 1990 Where: Arriving at the Los Angeles International Airport. Photo: 1990 Ron Galella, Ltd.
February 8, 1990 Where: With Johnny Depp at the NATO/ShoWest Convention in Las Vegas, Nevada. Photo: 1990 Ron Galella, Ltd.
Circa 1990 Where: With Bob Hoskins, and Christina Ricci in Mermaids. Photo: 2012 Getty Images
Circa 1990 Where: With Johnny Depp in Edward Scissorhands. Photo: 2012 Getty Images
August 11, 1989 Where: On Set for "Debbie Gibson Is Pregnant with My Two-Headed Love Child" the Music Video
August 3, 1989 Where: At the Sex, Lies, and Videotape premiere. Photo: 1989 Ron Galella, Ltd.
July 21, 1989 Where: At the Twelfth Night or What You Will Off-Broaday Play Performance in New York City. Photo: 1989 Ron Galella, Ltd.
June 26, 1989 Where: At the Great Balls of Fire New York City Premiere. Photo: 1989 Ron Galella
June 19, 1989 Where: At the Batman premiere. Photo: 1989 Ron Galella, Ltd.
April 29, 1989 Where: At Damien Elwes' Art Exhibtion in West Hollywood, California. Photo: 1989 Ron Galella, Ltd.
April 24, 1989 Where: At the Athletes Entertainers Kids Benefit.
March 29, 1989 Where: With Christian Slater at the Shrine Auditorium in Los Angeles, California.
March 25, 1989 Where: At the Independent Spirit Awards in Hollywood, California. Photo: 1989 Ron Galella, Ltd.
February 22, 1989 Where: At a GRAMMY Awards After Party.
January 23, 1988 Where: With Rob Lowe at the Golden Globe Awards.
Circa 1988 Where: With Shannen Doherty, Lisanne Falk and Kim Walker on set of the film Heathers. Photo: 2012 Getty Images
March 26, 1987 Where: With Michael Nesmith at the premiere party for Amazing Grace and Chuck in Hollywood, California. Photo: 1987 Ron Galella, ...
March 26, 1987 Where: With Michael Nesmith at the premiere party for Amazing Grace and Chuck in Hollywood, California. Photo: 1987 Ron Galella, Ltd.
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