Winona Ryder ruled the 90s with fan-favorite films, including Reality Bites, Little Women, Edward Scissorhands, Mermaids, and Girl Interrupted. Ryder stood apart from the other 90s actresses thanks to her penchant for playing outcasts like freaks, geeks, and rejects, though she also showed considerable talent in more conventional dramatic parts. She was also mysterious and, therefore, one of the trendiest girls of the ’90s.
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Her chic androgyny never failed to make a statement. The two-time Oscar nominee was the undeniable queen of grunge in the ’90s, with her characteristic chokers, slip dresses, blazers, and cardigans, as well as bandanas, biscuit-colored chinos, mules, and cocoa-toned jackets. Let’s take a stroll down memory lane and see some of Winona Ryder’s most iconic outfits from the ’80s and ’90s.
Winona Ryder Was An Icon Of Ethereal Beauty And Satin In The Late 1980s
Winona Ryder, then relatively unknown, looked stunning in a satin slip dress and an oversized blazer at the Athletes and Entertainers for Kids Foundation All-Star Tribute to Kareem Abdul-Jabbar on April 24, 1989, at Century Plaza Hotel in Los Angeles, California. Now fast-forward to 2019; this is the fashion set’s standard attire.
For the “Great Balls of Fire” Premiere on June 26, 1989, at the Ziegfeld Theater in New York City, the actress channeled her Heathers character by donning an off-the-shoulder white dress with sheer long sleeves, stockings, and adorable kitten heels.
Winona Ryder’s Airport Chic And Edward Scissorhands Premiere Monochromatic Black Look Set The None For Her 1990 Style Dominance
Arriving for her trip looking effortlessly sleek and androgynous, Winona Ryder disproved the stereotype that airports are places to look disheveled and harried.
The young actress, who was always one step ahead of the fashion curve, wore a masculine suit with dress shoes, big ankle socks, and an oversized white t-shirt to play up the part. That ’70s duffel bag perfectly sealed her impeccable taste status.
Showing 1990 was her style year, Winona attended the Edward Scissorhands premiere in 1990 in all black with then-boyfriend and co-star Johnny Depp, who also wore all black. Ryder embodied every resurgent ’90s fashion trend, from the sheer details of her clothing to the scarlet lipstick on her lips and the fringe on her purse.
The Year Is 1991, And Winona Shows No Signs Of Slowing Down
One of the most recognizable looks of the 1990s belongs to the ensemble Ryder wore to the 1991 musical comedy-drama The Commitments premiere. From Tumblr mood boards to your current Instagram feed, the fit has undoubtedly crossed your path more than once, and you’ve probably worn a version of this look too.
This outfit of a vintage band tee, a lapel-studded leather jacket, and a pair of light-wash mom jeans is as classic as it gets and just as desirable. Recently, Winona wore the same Tom Waits T-shirt she wore in the ’80s to the press junket for Destination Wedding in 2018.
Proving pants are just as stylish as dresses, Winona wore a beautiful brown suit to the premiere of Little Man Tate in 1991. Another suit, worn by Winona Ryder to the premiere of Backdraft in 1991, stood out among the many others she wore because of its monochrome color scheme and late-80s severe proportions. Fast-forward to 2020 at the SAG Awards, Winona wore a deconstructed blazer over an elaborate ballgown, proving that she remains a significant figure in red carpet suits long after the 1990s.
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Expanding Her Repertoire To include Lighter, More Airy Styles
Winona was well-known for her penchant for dark clothing that included a touch of leather and a fierce red lip. However, she typically opted for much lighter, airier outfits when walking the red carpet at The Academy Awards. She often attended as a leading lady and was nominated twice for her performances in Little Women and The Age of Innocence.
Here, at the 66th annual academy awards show in 1994, dressed in a dreamy off-white beaded outfit with a fringed skirt and a soft shawl, reminiscent of the styles of flappers of the 1920s. Two years later, she wore another beaded gown, this time with a bustier and a perfect finger-waved ‘do, taking the Roaring Twenties concept even further.
And who could forget that jaw-dropping number at the 57th annual Golden Globes? Winona wore a white v-neck dress with embellishments to the awards show, accompanied by her then-boyfriend, Matt Damon.
Maintaining A Cute And Flirty Tone Style
Ryder wore a lace dress reminiscent of Audrey Hepburn’s at the American Movie Classics 5th Anniversary Film Preservation Festival in 1997, proving that she didn’t wholly shun feminine attire despite her preference for tomboyish fashion.
Keeping up her feminine streak, Ryder was seen in a light blue dress with a boatneck for the 1998 premiere of Smoke Signals, marking another rare instance of the actress donning color.
