Winona Ryder: 25 Years of Red-Carpet Looks
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.
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.
Photo: Ron Galella
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.
Photo: Ron Galella, Ltd./1989 Ron Galella, Ltd.
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.
Photo: Ron Galella, Ltd./1989 Ron Galella, Ltd.
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?)
Photo: Ron Galella, Ltd./1990 Ron Galella, Ltd.
Wino forever.
Photo: Barry KingHere 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?
Photo: Barry King/2003 WireImageOkay, let's not talk about the pantyhose anymore. Especially when we can talk about Johnny Depp's ensemble.
Photo: Jim SmealLeather jacket.
Photo: Ron Galella, Ltd./1991 Ron Galella, Ltd.Leather jacket, severe black hair.
Photo: Ron Galella, Ltd./1992 Ron Galella, Ltd.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!
Photo: Ron Galella, Ltd./1992 Ron Galella, Ltd.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?)
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.
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.
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.
Photo: Vinnie ZuffanteIs that white hose peeking out?! Nooooo.
Photo: Ron GalellaAt the Oscars, where Ryder was nominated for her role in Little Women.
Photo: Vince BucciWait, actually this is the entire nineties summed up in one photo. "Yes, children, we really did wear shoes like that!"
Photo: Jim SmealAt the Oscars again.
Photo: Vince BucciWith Giorgio Armani.
Photo: New York Daily News Archive/1996/Daily News, L.P. (New York)So many coats.
Photo: Evan AgostiniClaire Danes, again with her red barette.
Photo: Ron Galella, Ltd./1996 Ron Galella, Ltd.More coats!
Photo: Frank Trapper/? Corbis. All Rights Reserved.DAYUM.
Photo: Frank Trapper/? Corbis. All Rights Reserved.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.
Photo: Ronald Siemoneit/? Corbis. All Rights Reserved.It's okay to miss short-hair-era, pre-Goop Gwyneth, yes?
Photo: Jim SmealAgain with the perfect pixie cut.
Photo: Mitchell Gerber/? Corbis. All Rights Reserved.Leather skirt.
Photo: Ronald Siemoneit/? Corbis. All Rights Reserved.Gwyneth Patlrow was in five movies in 1998.
Photo: KMazurEmbracing ethereal drapeyness with Chiara Mastroianni at Cannes.
Photo: Cardinale-Robert/? Corbis. All Rights Reserved.A rare jewel tone!
Even in a weird photo with Billie Joe Armstrong, Winona Ryder still looks goddamn adorable.
Photo: Jeff Kravitz/@2005 Jeff Kravitz/FilmMagic.comWe can't tell if she has a bunch of black-cord chokers, or just one that she really likes.
Photo: Kevin Mazur ArchiveMore chokers.
Photo: Ron Galella, Ltd./1998 Ron Galella, Ltd.Fancier choker.
Photo: ? Corbis. All Rights Reserved.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.
Photo: Steve GranitzOh, sad.
Photo: Sam LeviWith Kevin Haley. That black headband is going to become iconic in a few years.
Photo: Ke.MazurThis happened?!
Photo: KMazurSo shaggy.
Photo: Evan AgostiniThere's something jarring about Winona Ryder as a blonde.
Photo: Getty ImagesThe leather jacket does not count because Kevin Spacey is wearing it.
Photo: Frank MicelottaAnother jacket! And another shot with Kevin Haley.
Photo: Chris WeeksBlonde wavy hair and a shiny gold dress: Not the Winona looks we've come to expect.
Photo: Chris Weeks/Getty ImagesBookmark this photo, so on bad days you can revisit it and feel joy.
Photo: Richard Corkery/NY Daily News Archive via Getty ImagesAt the MTV Movie Awards, where the dress code is casual. No, more casual. Even more casual!
Photo: Kevin WinterHow should defendants dress? In Marc Jacobs, mostly, though less visible undergarments are our friends.
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.
Coat enthusiasm intact!
Reality Bites reunion, with coat.
Photo: Frazer Harrison/2004 Getty ImagesPrim!
Less prim!
Photo: Peter Kramer/2006 Getty ImagesThe woman likes a round-toe pump.
Photo: Mark Mainz/2006 Getty ImagesWith Marc Jacobs and Robert Duffy, and coat.
(She's carrying a coat in her hand!)
With Al Pacino, and Al Pacino's hair.
Photo: Kevin Winter/2007 Getty ImagesYukking it up with noted laughmeister Sean Penn.
Photo: Eric CharbonneauWith Pink and Juliette Lewis, of course.
Photo: Jason Merritt/2008 FilmMagicReturn of the choker! And a Mermaids reunion.
With Tim Burton, aw.
Photo: Kevin Winter/2008 Getty ImagesSo many of-a-kind black dresses.
Photo: Vittorio Zunino Celotto/2009 Getty Images
Even similar formal black dresses!
But just one black suit.
Photo: Michael Loccisano/2010 Getty ImagesAt the SAG awards for Black Swan.
Photo: Jason Merritt/2011 Getty ImagesCoat dress!
Photo: Jason Merritt/2012 Getty ImagesSimplicity!
Photo: A-way! / Splash News/???? www.splashnews.comGreen!
Photo: Jason Merritt/2012 Getty ImagesThose are some seriously precarious shoes. Be careful out there, Winona.