Winona Ryder arrives to the 45th Annual Golden Globe awards in January, 1988 with Rob Lowe on her arm, wearing a ladylike black and red dress, classic black leather pumps and modest sheer black stockings.
The actress attended the 'Great Balls of Fire' New York City premiere in June, 1989 wearing a very modern white off-the-shoulder bodycon dress with white sheer stockings.
Winona Ryder wore a chic little black wrap dress, crimson lip and her ladylike pumps to the 48th Annual Golden Globes in January 1991 with boyfriend Johnny Depp.
Winona Ryder attends the 'Dracula' Hollywood premiere in November 1992 dressed in a cornflower blue button down top and matching skirt with a white lace trim.
Winona Ryder wore a cute pixie cut a purple velvet slip dress at the The Age of Innocence' New York City premiere in September 1993 with long-haired musician Dave Pirner of Soul Asylum.
At the 1996 Academy Awards, Winona Ryder epitomized Hollywood glam in this vintage deep-cut nude gown with matching shawl and nude satin heels.
The actress wire a white floral satin frock with matching mules at the American Movie Classics' Fourth Annual Film Preservation Festival in 1996.
Winona Ryder arrived to the premiere of the film 'The Crucible’ wearing a black ankle-grazing dress and midnight blue wool statement coat with black fur trim in 1996.
At the 1997 Vanity Fair Oscar party, Winona Ryder embraced the flapper look by pairing a beaded gown with a crimson lip.
At the AMC’s 5th Annual Preservation Festival in 1997, Winona Ryder looked stunning in a ‘50s-inspired pale lavender lace dress and black peep toe heels.
The actress was simple and chic in a black leather pencil skirt, mock short-sleeved turtleneck and scrappy mule sandals at the the 'Alien: Resurrection' Westwood premiere in 1997.
Winona Ryder looked youthful and fresh at the premiere of ‘Smoke Signals’ in New York wearing a periwinkle blue frock and basic strap metallic sandals in 1998.
After spending a few years out of the spotlight, Winona Ryder reemerged at the 19th Annual Museum of the Moving Image Benefit in 2004 wearing a gorgeous off-the-shoulder crimson gown with a sweetheart neckline.
Winona Ryder was eclectic and at the 'Before Sunset' premiere at the Los Angeles Film Festival in 2004.
The actress attended the 35th Annual AFI Life Achievement Award Gala in 2007 wearing a dazzling vintage tea-length Christian Dior dress with jewel-covered pumps.
For the Los Angeles closing night premiere of ‘Black Swan’ in 2010, Winona Ryder wore a black strapless ankle-grazing dress with a voluminous skirt.
Winona Ryder looked like a princess in this cream Alberta Ferretti gown at the 17th Annual Screen Actors Guild Awards in 2011.
For ‘The Iceman’ premiere during the 69th Venice Film Festival in 2012, Winona Ryder look effortlessly chic in a strapless black lace Dolce & Gabbana gown and blood orange lip.
Winona Ryder attended the New York premiere of her HBO miniseries ‘Show Me a Hero’ wearing a black and white velvet Oscar de la Renta dress in 2015.
The actress wore a sexy satin Marc Jacobs LBD on the red carpet before at New York Fashion Week in 2015.