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90s nostalgia
March 27, 2013

Winona Ryder: 25 Years of Red-Carpet Looks

By Margaret Lyons, Maya Robinson

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Photo: Ron Galella, Ltd./Getty1989 Ron Galella, Ltd.

Beetlejuice came out 25 years ago this week. It’s the movie that put Winona Ryder on the map — before Heathers, before Edward Scissorhands, and well before Reality Bites. Since then, Ryder’s been a steady pop-culture presence, the best ambassador for short hair since Mia Farrow and the most fashionable criminal defendant in living memory. (She’s also dated a notable guy or two.) Let’s look back through a quarter century of Winona Ryder photos, shall we?

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1 / 77 Photos
Age 15. An age where perms seem like a totally reasonable idea. Age 15. An age where perms seem like a totally reasonable idea.

Age 15. An age where perms seem like a totally reasonable idea.

Photo: LGI Stock/? Corbis. All Rights Reserved.
With Rob Lowe at the Golden Globes. They co-starred in Square Dance, which earned Lowe a Golden Globe nomination. With Rob Lowe at the Golden Globes. They co-starred in Square Dance, which earned Lowe a Golden Globe nomination.

With Rob Lowe at the Golden Globes. They co-starred in Square Dance, which earned Lowe a Golden Globe nomination.

Photo: Ron Galella
At the Oscars with Heathers co-star Christian Slater. Fuck me gently with a chainsaw. Either one of you. At the Oscars with Heathers co-star Christian Slater. Fuck me gently with a chainsaw. Either one of you.

At the Oscars with Heathers co-star Christian Slater. Fuck me gently with a chainsaw. Either one of you.

Photo: Darlene Hammond
The first of many leather jackets. The first of many leather jackets.

The first of many leather jackets.

Photo: Ron Galella, Ltd./1989 Ron Galella, Ltd.
The white hose is tough, but that dress is still cute. The white hose is tough, but that dress is still cute.

The white hose is tough, but that dress is still cute.

Photo: Ron Galella/1989 Ron Galella
Winona Ryder: Secretly a tiny child wearing dad clothes. Winona Ryder: Secretly a tiny child wearing dad clothes.

Winona Ryder: Secretly a tiny child wearing dad clothes.

Photo: Ron Galella, Ltd./1989 Ron Galella, Ltd.
Again, say no to white hose. Again, say no to white hose.

Again, say no to white hose.

Photo: Ron Galella, Ltd./1989 Ron Galella, Ltd.
With Johnny Depp and a leather jacket. (Same jacket, possibly? Just way more broken-in?) With Johnny Depp and a leather jacket. (Same jacket, possibly? Just way more broken-in?)

With Johnny Depp and a leather jacket. (Same jacket, possibly? Just way more broken-in?)

 

Photo: Ron Galella, Ltd./1990 Ron Galella, Ltd.
Wino forever. Wino forever.

Wino forever.

Photo: Barry King
Here they are at the premiere of Edward Scissorhands. Here they are at the premiere of Edward Scissorhands.

Here they are at the premiere of Edward Scissorhands.

Photo: Frank Trapper/? Corbis. All Rights Reserved.
How do two people get so pretty? At once? And stand with each other? How do two people get so pretty? At once? And stand with each other?

How do two people get so pretty? At once? And stand with each other?

Photo: Barry King/2003 WireImage
Okay, let's not talk about the pantyhose anymore. Especially when we can talk about Johnny Depp's ensemble. Okay, let's not talk about the pantyhose anymore. Especially when we can talk about Johnny Depp's ensemble.

Okay, let's not talk about the pantyhose anymore. Especially when we can talk about Johnny Depp's ensemble.

Photo: Jim Smeal
Leather jacket. Leather jacket.

Leather jacket.

Photo: Ron Galella, Ltd./1991 Ron Galella, Ltd.
Leather jacket, severe black hair. Leather jacket, severe black hair.

Leather jacket, severe black hair.

Photo: Ron Galella, Ltd./1992 Ron Galella, Ltd.
Still with the long hair... Still with the long hair...

Still with the long hair...

Photo: Mauro Carraro/? Corbis. All Rights Reserved.
Okay, sure, this outfit is very 1992. But look at that lady in the background! Okay, sure, this outfit is very 1992. But look at that lady in the background!

Okay, sure, this outfit is very 1992. But look at that lady in the background!

Photo: Ron Galella, Ltd./1992 Ron Galella, Ltd.
Ah, the dawn of the pixie cut! With Soul Asylum's Dave Pirner. Ah, the dawn of the pixie cut! With Soul Asylum's Dave Pirner.

Ah, the dawn of the pixie cut! With Soul Asylum's Dave Pirner.

Photo: Ron Galella, Ltd./1993 Ron Galella, Ltd.
With her Golden Globe for The Age of Innocence. (Might those be the same pearls she wore when she went to the Globes with Rob Lowe?) With her Golden Globe for The Age of Innocence. (Might those be the same pearls she wore when she went to the Globes with Rob Lowe?)

With her Golden Globe for The Age of Innocence. (Might those be the same pearls she wore when she went to the Globes with Rob Lowe?)

Photo: Steve Sta...

With her Golden Globe for The Age of Innocence. (Might those be the same pearls she wore when she went to the Globes with Rob Lowe?)

Photo: Steve Starr/? Corbis. All Rights Reserved.
At the premiere of Reality Bites. At the premiere of Reality Bites.

At the premiere of Reality Bites.

Photo: Ron Galella, Ltd./1994 Ron Galella, Ltd.
Here you go, it's the entire nineties, summed up in one photo. You're welcome! No further time-capsuling necessary. Here you go, it's the entire nineties, summed up in one photo. You're welcome! No further time-capsuling necessary.

Here you go, it's the entire nineties, summed up in one photo. You're welcome! No further time-capsuling necessary.

Photo: ? Corbis. All Rights Rese...

Here you go, it's the entire nineties, summed up in one photo. You're welcome! No further time-capsuling necessary.

Photo: ? Corbis. All Rights Reserved.
Velvet coats? There was a recent velvet coat era, apparently. Velvet coats? There was a recent velvet coat era, apparently.

Velvet coats? There was a recent velvet coat era, apparently.

Photo: Vinnie Zuffante
Is that white hose peeking out?! Nooooo. Is that white hose peeking out?! Nooooo.

Is that white hose peeking out?! Nooooo.

Photo: Ron Galella
At the Oscars, where Ryder was nominated for her role in Little Women. At the Oscars, where Ryder was nominated for her role in Little Women.

At the Oscars, where Ryder was nominated for her role in Little Women.

Photo: Vince Bucci
Wait, actually this is the entire nineties summed up in one photo. "Yes, children, we really did wear shoes like that!" Wait, actually this is the entire nineties summed up in one photo. "Yes, children, we really did wear shoes like that!"

Wait, actually this is the entire nineties summed up in one photo. "Yes, children, we really did wear shoes like that!"

Photo: Jim Smeal
At the Oscars again. At the Oscars again.

At the Oscars again.

Photo: Vince Bucci
With Giorgio Armani. With Giorgio Armani.

With Giorgio Armani.

Photo: New York Daily News Archive/1996/Daily News, L.P. (New York)
So many coats. So many coats.

So many coats.

Photo: Evan Agostini
Claire Danes, again with her red barette. Claire Danes, again with her red barette.

Claire Danes, again with her red barette.

Photo: Ron Galella, Ltd./1996 Ron Galella, Ltd.
More coats! More coats!

More coats!

Photo: Frank Trapper/? Corbis. All Rights Reserved.
DAYUM. DAYUM.

DAYUM.

Photo: Frank Trapper/? Corbis. All Rights Reserved.
Doing flapper-style proud ... Doing flapper-style proud ...

Doing flapper-style proud ...

Photo: Ronald Siemoneit/? Corbis. All Rights Reserved.
Those wedges are weird by today's standard, but truth: Everyone had those shoes in 1997. Those wedges are weird by today's standard, but truth: Everyone had those shoes in 1997.

Those wedges are weird by today's standard, but truth: Everyone had those shoes in 1997.

Photo: Ronald Siemoneit/? Corbis. All Rights Reserved.
It's okay to miss short-hair-era, pre-Goop Gwyneth, yes? It's okay to miss short-hair-era, pre-Goop Gwyneth, yes?

It's okay to miss short-hair-era, pre-Goop Gwyneth, yes?

Photo: Jim Smeal
Again with the perfect pixie cut. Again with the perfect pixie cut.

Again with the perfect pixie cut.

Photo: Mitchell Gerber/? Corbis. All Rights Reserved.
Leather skirt. Leather skirt.

Leather skirt.

Photo: Ronald Siemoneit/? Corbis. All Rights Reserved.
Gwyneth Patlrow was in five movies in 1998. Gwyneth Patlrow was in five movies in 1998.

Gwyneth Patlrow was in five movies in 1998.

Photo: KMazur
Embracing ethereal drapeyness with Chiara Mastroianni at Cannes. Embracing ethereal drapeyness with Chiara Mastroianni at Cannes.

Embracing ethereal drapeyness with Chiara Mastroianni at Cannes.

Photo: Cardinale-Robert/? Corbis. All Rights Reserved.
A rare jewel tone! A rare jewel tone!

A rare jewel tone!

Even in a weird photo with Billie Joe Armstrong, Winona Ryder still looks goddamn adorable. Even in a weird photo with Billie Joe Armstrong, Winona Ryder still looks goddamn adorable.

Even in a weird photo with Billie Joe Armstrong, Winona Ryder still looks goddamn adorable.

Photo: Jeff Kravitz/@2005 Jeff Kravitz/FilmMagic.com
We can't tell if she has a bunch of black-cord chokers, or just one that she really likes. We can't tell if she has a bunch of black-cord chokers, or just one that she really likes.

We can't tell if she has a bunch of black-cord chokers, or just one that she really likes.

Photo: Kevin Mazur Archive
More chokers. More chokers.

More chokers.

Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.
Fancier choker. Fancier choker.

Fancier choker.

Photo: ? Corbis. All Rights Reserved.
Still a cute dress! Still a cute dress!

Still a cute dress!

Photo: Ron Galella, Ltd./1999 Ron Galella, Ltd.
At the Golden Globes with boyfriend Matt Damon. The woman has dated some heart-throbs. At the Golden Globes with boyfriend Matt Damon. The woman has dated some heart-throbs.

At the Golden Globes with boyfriend Matt Damon. The woman has dated some heart-throbs.

Photo: Steve Granitz
Oh, sad. Oh, sad.

Oh, sad.

Photo: Sam Levi
With Kevin Haley. That black headband is going to become iconic in a few years. With Kevin Haley. That black headband is going to become iconic in a few years.

With Kevin Haley. That black headband is going to become iconic in a few years.

Photo: Ke.Mazur
This happened?! This happened?!

This happened?!

Photo: KMazur
So shaggy. So shaggy.

So shaggy.

Photo: Evan Agostini
There's something jarring about Winona Ryder as a blonde. There's something jarring about Winona Ryder as a blonde.

There's something jarring about Winona Ryder as a blonde.

Photo: Getty Images
The leather jacket does not count because Kevin Spacey is wearing it. The leather jacket does not count because Kevin Spacey is wearing it.

The leather jacket does not count because Kevin Spacey is wearing it.

Photo: Frank Micelotta
Another jacket! And another shot with Kevin Haley. Another jacket! And another shot with Kevin Haley.

Another jacket! And another shot with Kevin Haley.

Photo: Chris Weeks
Blonde wavy hair and a shiny gold dress: Not the Winona looks we've come to expect. Blonde wavy hair and a shiny gold dress: Not the Winona looks we've come to expect.

Blonde wavy hair and a shiny gold dress: Not the Winona looks we've come to expect.

Photo: Chris Weeks/Getty Images
Bookmark this photo, so on bad days you can revisit it and feel joy. Bookmark this photo, so on bad days you can revisit it and feel joy.

Bookmark this photo, so on bad days you can revisit it and feel joy.

Photo: Richard Corkery/NY Daily News Archive via Getty Images
At the MTV Movie Awards, where the dress code is casual. No, more casual. Even more casual! At the MTV Movie Awards, where the dress code is casual. No, more casual. Even more casual!

At the MTV Movie Awards, where the dress code is casual. No, more casual. Even more casual!

Photo: Kevin Winter
How should defendants dress? In Marc Jacobs, mostly, though less visible undergarments are our friends. How should defendants dress? In Marc Jacobs, mostly, though less visible undergarments are our friends.

How should defendants dress? In Marc Jacobs, mostly, though less visible undergarments are our friends.

Coat and headband, the definitive court ensemble. Coat and headband, the definitive court ensemble.

Coat and headband, the definitive court ensemble.

Photo: ? Corbis. All Rights Reserved.
After some time away from the spotlight, Ryder reemerged, looking pretty darn gorgeous. After some time away from the spotlight, Ryder reemerged, looking pretty darn gorgeous.

After some time away from the spotlight, Ryder reemerged, looking pretty darn gorgeous.

Coat enthusiasm intact! Coat enthusiasm intact!

Coat enthusiasm intact!

Reality Bites reunion, with coat. Reality Bites reunion, with coat.

Reality Bites reunion, with coat.

Photo: Frazer Harrison/2004 Getty Images
Prim! Prim!

Prim!

Less prim! Less prim!

Less prim!

Photo: Peter Kramer/2006 Getty Images
The woman likes a round-toe pump. The woman likes a round-toe pump.

The woman likes a round-toe pump.

Photo: Mark Mainz/2006 Getty Images
With Marc Jacobs and Robert Duffy, and coat. With Marc Jacobs and Robert Duffy, and coat.

With Marc Jacobs and Robert Duffy, and coat.

(She's carrying a coat in her hand!) (She's carrying a coat in her hand!)

(She's carrying a coat in her hand!)

 

With Al Pacino, and Al Pacino's hair. With Al Pacino, and Al Pacino's hair.

With Al Pacino, and Al Pacino's hair.

Photo: Kevin Winter/2007 Getty Images
Yukking it up with noted laughmeister Sean Penn. Yukking it up with noted laughmeister Sean Penn.

Yukking it up with noted laughmeister Sean Penn.

Photo: Eric Charbonneau
With Pink and Juliette Lewis, of course. With Pink and Juliette Lewis, of course.

With Pink and Juliette Lewis, of course.

Photo: Jason Merritt/2008 FilmMagic
Return of the choker! And a Mermaids reunion. Return of the choker! And a Mermaids reunion.

Return of the choker! And a Mermaids reunion.

With Tim Burton, aw. With Tim Burton, aw.

With Tim Burton, aw.

Photo: Kevin Winter/2008 Getty Images
So many of-a-kind black dresses. So many of-a-kind black dresses.

So many of-a-kind black dresses.

 

Photo: Vittorio Zunino Celotto/2009 Getty Images
Even similar formal black dresses! Even similar formal black dresses!

Even similar formal black dresses!

But just one black suit. But just one black suit.

But just one black suit.

Photo: Michael Loccisano/2010 Getty Images
At the SAG awards for Black Swan. At the SAG awards for Black Swan.

At the SAG awards for Black Swan.

Photo: Jason Merritt/2011 Getty Images
Coat dress! Coat dress!

Coat dress!

Photo: Jason Merritt/2012 Getty Images
Simplicity! Simplicity!

Simplicity!

Photo: A-way! / Splash News/???? www.splashnews.com
Green! Green!

Green!

Photo: Jason Merritt/2012 Getty Images
Those are some seriously precarious shoes. Be careful out there, Winona. Those are some seriously precarious shoes. Be careful out there, Winona.

Those are some seriously precarious shoes. Be careful out there, Winona.

1 / 77

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