Winona Ryder: 25 Years of Red-Carpet Looks - Slideshow - Vulture

March 27, 2013 11:00 am

Winona Ryder: 25 Years of Red-Carpet Looks

By Margaret Lyons, Maya Robinson

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?

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

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

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.

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.

The first of many leather jackets.

The first of many leather jackets.

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

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

Winona Ryder: Secretly a tiny child wearing dad clothes.

Winona Ryder: Secretly a tiny child wearing dad clothes.

Again, say no to white hose.

Again, say no to white hose.

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?)

Wino forever.

Wino forever.

Here they are at the premiere of Edward Scissorhands.

Here they are at the premiere of Edward Scissorhands.

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?

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.

Leather jacket.

Leather jacket.

Leather jacket, severe black hair.

Leather jacket, severe black hair.

Still with the long hair...

Still with the long hair...

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!

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.

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?)

At the premiere of Reality Bites.

At the premiere of Reality Bites.

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.

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

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

Is that white hose peeking out?! Nooooo.

Is that white hose peeking out?! Nooooo.

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.

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!"

At the Oscars again.

At the Oscars again.

With Giorgio Armani.

With Giorgio Armani.

So many coats.

So many coats.

Claire Danes, again with her red barette.

Claire Danes, again with her red barette.

More coats!

More coats!

DAYUM.

DAYUM.

Doing flapper-style proud ...

Doing flapper-style proud ...

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.

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

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

Again with the perfect pixie cut.

Again with the perfect pixie cut.

Leather skirt.

Leather skirt.

Gwyneth Patlrow was in five movies in 1998.

Gwyneth Patlrow was in five movies in 1998.

Embracing ethereal drapeyness with Chiara Mastroianni at Cannes.

Embracing ethereal drapeyness with Chiara Mastroianni at Cannes.

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.

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.

More chokers.

More chokers.

Fancier choker.

Fancier choker.

Still a cute dress!

Still a cute dress!

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.

Oh, sad.

Oh, sad.

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.

This happened?!

This happened?!

So shaggy.

So shaggy.

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

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

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

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

Another jacket! And another shot with Kevin Haley.

Another jacket! And another shot with Kevin Haley.

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.

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.

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!

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.

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!

Reality Bites reunion, with coat.

Reality Bites reunion, with coat.

Prim!

Prim!

Less prim!

Less prim!

The woman likes a round-toe pump.

The woman likes a round-toe pump.

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!)

With Al Pacino, and Al Pacino's hair.

With Al Pacino, and Al Pacino's hair.

Yukking it up with noted laughmeister Sean Penn.

Yukking it up with noted laughmeister Sean Penn.

With Pink and Juliette Lewis, of course.

With Pink and Juliette Lewis, of course.

Return of the choker! And a Mermaids reunion.

Return of the choker! And a Mermaids reunion.

With Tim Burton, aw.

With Tim Burton, aw.

So many of-a-kind black dresses.

So many of-a-kind black dresses.

Even similar formal black dresses!

Even similar formal black dresses!

But just one black suit.

But just one black suit.

At the SAG awards for Black Swan.

At the SAG awards for Black Swan.

Coat dress!

Coat dress!

Simplicity!

Simplicity!

Green!

Green!

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

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

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