Fashion
Winona Ryder’s Best ‘90s Fashion Moments
She did no wrong.
The ‘90s are very much back in fashion. While some people who are stocking up on baggy jeans and oversized blazers weren’t even alive during the sartorially inspiring decade, Winona Ryder remembers it well. The actor was all over the red carpet back then, and her ‘90s style will forever be on the radar of fashion fans.
“It’s hard to talk about the influence of the ‘90s because I lived through it, so I see it differently than the younger generation,” Ryder told Harper’s Bazaar back in 2018. “People are obviously carefully cherry picking the better trends — there were a lot of bad looks in the ‘90s.”
It’s not just the styles of the ‘90s that are enjoying a resurgence, but the shopping habits, too. Vintage and thrifting are very much back, as well, with online marketplaces including Depop and ThredUP making secondhand shopping easier than ever.
“There were certain things that were simply welcome — like, suddenly it was ‘cool’ to wear thrift store clothes, flannels, etc. That was great in the sense that it was something that everyone could afford,” she said. “I thought that was really cool. Then designers started making $500 flannel shirts and we were like, ‘huh?’”
While Ryder may have mixed feelings about old photos of her popping up on the mood boards of Gen Z, there is one thing that’s certain: She was, is, and always will be a ‘90s style icon. Below, check out some of her best looks from the decade.
1991, Backdraft premiere
Wearing a baggy black suit to the Backdraft premiere in 1991.
1991, The Commitments premiere
Wearing a leather jacket and straight-leg jeans to the premiere of The Commitments in 1991.
1991, Little Man Tate premiere
Wearing a baggy brown suit to the premiere of Little Man Tate in 1991.
1992, Night on Earth premiere
Wearing a leather jacket and black dress to the 1992 premiere of Night on Earth.
1992, Dracula premiere
Wearing a corset top and silk skirt to the Dracula premiere in 1992.
1993, The Age of Innocence premiere
Wearing a velvet dress to the premiere of Age of Innocence in 1993.
1994, Golden Globes
Wearing a black dress to the 1994 Golden Globes.
1994, Oscars
Wearing a white fringe gown to the 1994 Oscars.
1996, Vanity Fair Oscar Party
Wearing an embellished blush gown to the 1996 Vanity Fair Oscar Party.
1996, American Movie Classics' Film Preservation Festival
Wearing a floral-print satin dress to the 1996 American Movie Classics' Film Preservation Festival.
1996, The Crucible premiere
Wearing a black dress and fur-lined coat to the 1996 premiere of The Crucible.
1997, Vanity Fair Oscar Party
Wearing an embellished black gown to the 1997 Vanity Fair Oscar Party.
1997, AFI Lifetime Achievement Award Salute to Martin Scorsese
Wearing a strappy pink gown to the AFI Lifetime Achievement Award Salute to Martin Scorsese in 1997.
1997, Leaving LAX
Wearing black trousers and sneakers at LAX in 1997.
1997, American Movie Classics Film Preservation Festival
Wearing a lace-trimmed floral dress to the 1997 American Movie Classics Film Preservation Festival.
1997, Alien: Resurrection premiere
Wearing a leather skirt and short-sleeved turtleneck to the 1997 premiere of Alien: Resurrection.
1998, Joan of Arc 50th Anniversary Screening
Wearing a black dress and black-and-white coat to the 1998 Joan of Arc 50th anniversary screening.
1998, Film Society of Lincoln Center Honors Martin Scorsese
Wearing a sheer lace gown to the 1998 Film Society of Lincoln Center Honors Martin Scorsese event.
1998, Smoke Signals premiere
Wearing a blue dress and silver sandals to the 1998 premiere of Smoke Signals.
1998, MTV Movie Awards
Wearing a black tank top, pants, and thong flip-flops to the 1998 MTV Movie Awards.
1999, Golden Globes
Wearing an embellished white gown to the 1999 Golden Globes.
1999, Eyes Wide Shut premiere
Wearing a sheer-sleeved black dress to the premiere of Eyes Wide Shut in 1999.
1999, Girl, Interrupted premiere
Wearing a black skirt and sheer top to the 1999 premiere of Girl, Interrupted.
See more ‘90s fashion moments from Brandy, Mariah Carey, and Pamela Anderson and Tommy Lee.
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