Winona Ryder's Most Memorable Fashion Moments
Last week it was announced that Winona Ryder was coming back in a big way—as the star of Rag & Bone’s fall/winter 2014 campaign. The doe-eyed actress first hit the Hollywood scene in 1986's Lucas and has gone on to star in cult film classics like Heathers, Edward Scissorhands, and Reality Bites, as well as critically acclaimed movies including Girl, Interrupted and Black Swan. And along the way, she made waves with her evolving sartorial choices. As the ultimate '90s It girl, Ryder initially caught the public's attention with her tomboyish style, but her uniquely chic taste kept us coming back for more.
Though Ryder clearly prefers to wear black on the red carpet, she infuses her wardrobe with a variety of styles in the color. From girly to goth to grunge, the star has tried every look in the book. Never one to ignore a trend, Ryder has rocked oversized blazers, velvet slip dresses, leather jackets, LBDs, headbands, dazzling gowns, and menswear-inspired pieces over the years. A pop culture icon in her own right, the actress has worn some of fashion's biggest names including Dolce & Gabbana, Marc Jacobs, Christian Dior, and Givenchy, all while dating some of Hollywood's hottest leading men, like Rob Lowe, Johnny Depp (who can forget his infamous "Winona Forever" tattoo?), and Matt Damon.
September 8, 2016
Ryder chose a short-sleeve bespeckled black Givenchy by Ricardo Tisci dress for Tim Burton's Hand and Footprint Ceremony.
July 11, 2016
Ryder wore a floor-length dress with a satin sash and a matching coat for the premiere of Stranger Things.
August 11, 2015
For the New York premiere of her HBO miniseries Show Me a Hero, the actress chose a black and white velvet dress from Oscar de la Renta's fall 2013 collection.
January 11, 2014
Ryder chose a vintage-inspired LBD to attend the 3rd Annual Sean Penn & Friends Help Haiti Home Gala. She completed her look with black accessories and curled tresses.
November 20, 2013
The actress kept it simple in a chic Cushnie et Ochs frock that featured cutouts and a high neck at the premiere of Homefront in Las Vegas. She styled the head-to-toe black look with Armani pumps and a Louboutin clutch.
August 31, 2013
Ryder showed off her eccentric style at the 2013 US Open in a layered maxidress, chunky black shoes, and a woven peaked hat.
April 29, 2013
Ryder stepped out for a screening of her film The Iceman in New York City in a fit-and-flare little black dress. She topped her look off with a bold red lip and retro hairstyle.
April 22, 2013
For a screening of The Iceman in Los Angeles, the star looked chic and polished in a deep red frock, voluminous ponytail, and contrasting emerald jewels.
August 30, 2012
For The Iceman premiere during the 69th Venice Film Festival, Ryder dazzled in a lace Dolce & Gabbana gown and bejewelled Lanvin drop earrings.
February 17, 2012
Ryder attended the launch of Marni for H&M in a full look from the collaboration, which included a polka dot coat and cropped trousers.
January 30, 2011
Ryder was ethereal and sophisticated in a white Alberta Ferretti gown at the 17th Annual Screen Actors Guild Awards.
November 30, 2010
For the New York City premiere of Black Swan, Ryder caught everyone’s attention in a menswear-inspired black Givenchy suit. She completed her look with a statement necklace and drop earrings.
November 29, 2010
Ryder celebrated at IFP's 20th Annual Gotham Independent Film Awards in a beautiful Dolce & Gabbana lace strapless dress with a full skirt and pointed pumps.
May 4, 2009
At the 2009 Costume Institute Gala at The Metropolitan Museum of Art Ryder wowed in a one-sleeve minidress, which she paired with all-black accessories including tights, pumps, and a clutch.
June 07, 2007
The actress dazzled in a vintage tea-length Christian Dior dress and jewel-adorned pumps at the 35th Annual AFI Life Achievement Award Gala.
May 07, 2007
For the 2007 Met Gala, the icon wore a black Marc Jacobs gown featuring an oversized asymmetrical bow.
March 17, 2005
Ryder attended a party welcoming designer Marc Jacobs to Los Angeles in a flirty satin and lace frock by the label.
June 23, 2004
The actress arrived at the Los Angeles Film Festival Premiere of Before Sunset in an artistic print dress and red patterned overcoat.
April 20, 2004
At the 19th Annual Museum of the Moving Image Benefit, the actress stunned in an off-the-shoulder crimson gown with a sweetheart neckline.
September 6, 2003
The actress wore a pretty black-and-white dress to a gallery exhibition opening in New York City that she paired with simple pumps and a sleek hairdo.
January 23, 2000
The actress looked lovely next to Matt Damon on the red carpet in an embellished white gown at the 57th Annual Golden Globe Awards.
June 23, 1998
Ryder looked fresh in a periwinkle blue frock and metallic sandals for the premiere of Smoke Signals in New York City.
May 4, 1998
For an event at Lincoln Center in New York City, the icon glowed in a sparkling semi-sheer black gown complete with matching wrap and bold red lip.
September 25, 1997
At AMC's 5th Annual Preservation Festival, the actress looked beautiful in a pale lavender dress covered in black lace. She styled the ensemble with peep toe heels, a black clutch, and dazzling diamond jewelry.
February 20, 1997
Ryder attended the 25th Annual American Film Institute Lifetime Achievement Award Gala in a wow-worthy satin pink gown with her hair cut into her once-signature pixie.
March 25, 1996
Ryder epitomized old Hollywood glamour at the 1996 Academy Awards in a low-cut nude gown with matching shawl and satin heels. The star styled her pixie in retro waves, and topped off the look with major diamond earrings.
March 21, 1994
Ryder made a statement at the Oscars in this figure-hugging cream gown that was covered in delicate beads and finished with a long fringe hem.
November 10, 1992
Ryder stepped out for the Dracula premiere at Mann's Chinese Theatre in Hollywood wearing a dark cornflower blue skirt and top with a white lace trim.
January 19, 1991
The star attended the 48th Annual Golden Globe Awards with Johnny Depp in a black wrap dress and bright crimson lip.
April 29, 1989
At the Damien Elwes' Art Exhibtion at the CAZ Gallery in West Hollywood, Ryder rocked a denim miniskirt over tights and a cool black leather jacket.