Winona Ryder has always been the Hollywood’s definitive ‘90s goth chick, and as a young actress, she thrived while playing edgy characters in Beetlejuice, Heathers, Edward Scissorhands, Reality Bites and Girl Interrupted. On the red carpet, that theme continued, as she embraced mostly black whenever attending premieres for those movies, or the award shows where she was nominated for her roles. There were a few occasions when the actress would dabble in color, but nine times out of ten, Ryder stuck to her tried-and-true gothic hue. As the years went on, Ryder seemingly became even more loyal to black, embracing variety in the form of texture with lace, embellishments, and sometimes even tulle. The actress has often worn designer, but she’s also known for being quite the vintage lover, even once admitting she wore a $10 dress to the Academy Awards. She also isn’t afraid to rewear a look. “I know that’s kind of a no-no in the fashion world, but why wear something just once if you love it?” she said, and that’s just one of the many reasons why we love her. Now, in honor of her 51st birthday, we’re taking a look back at her most iconic red carpet moments from the past thirty years.
2022: Stranger Things Season 4 Premiere
Ryder wore a slightly-oversized three-piece suit with pants that pooled at her feet to the premiere of Stranger Things season four. She accessorized the ensemble with a black bag and a pin of her own character, Joyce Byers, on her lapel.
2020: The Plot Against America Premiere
The actress paired her dark blue Christian Dior fall 2018 haute couture long-sleeve dress with the Philip Roth book, Plot Against America, on which the TV series was based.
2020: Screen Actors Guild Awards
Ryder merged suit tailoring with feminine tulle in this Christian Dior spring 2018 haute couture dress at the 2020 SAG Awards.
2019: Stranger Things Season 3 Premiere
Sticking to her favorite color, Ryder wore a black tea-length dress with a boatneck to the season three premiere of her hit Netflix show.
2018: Screen Actors Guild Awards
Ryder paired a black, floor-length dress with a blazer and satin clutch at the 24th annual SAG Awards.
2017: Stranger Things Season 2 Premiere
Wearing an empire-waist gown with a bow detail, Ryder attended the season two premiere of Stranger Things.
2017: Screen Actors Guild Awards
Ryder wore a Ryan Roche black lace gown with a large heart pendant to the 2017 SAG Awards.
2017: Golden Globe Awards
The actress brought a touch more glamour to the Golden Globes in 2017, wearing a strapless Viktor & Rolf dress on the red carpet.
2016: Stranger Things Premiere
Ryder loves to pair a blazer with a dress, which is what she did at the premiere of Stranger Things back in 2016.
2015: Show Me a Hero Premiere
Not quite color, but something other than black. Ryder wore a mid-length Oscar de la Renta fall 2013 dress covered in white lace to the premiere of Show Me a Hero in 2015.
2012: Venice International Film Festival
Ryder wore a black lace Dolce & Gabbana gown with Lanvin earrings to the premiere of her film, The Iceman, at the Venice International Film Festival.
2010: Screen Actors Guild Awards
Leave it to Ryder to bring some edge to a wedding dress. The actress styled this Alberta Ferretti spring 2011 bridal gown with a messy updo, heavily-lined eyes, and a black purse at the 17th annual SAG Awards.
2010: Black Swan Premiere
What’s more fitting than wearing a dress with a tulle skirt to a premiere for a film about ballet?
2009: Met Gala
The actress wore an off-the-shoulder LBD to “The Model as Muse: Embodying Fashion” Costume Institute Gala in 2009.
2007: Met Gala
Ryder attended the 2007 Met Gala on the arm of Marc Jacobs, so it’s only fitting she wore a dress by the designer.
2006: Vanity Fair Oscar Party
Wearing a mid-length, black dress with a black shawl, Ryder attended the Vanity Fair Oscar party with then-boyfriend, filmmaker Henry Alex-Rubin.
2004: Before Sunset Premiere
It’s a bit shocking to see Ryder in so much color, but the actress looked great in this colorful, boho ensemble at the Before Sunset premiere in 2004.
2001: Academy Awards
Ryder wore a greenish-gold strapless dress covered in embellishments to the Oscars in 2001, which she attended with her date, Kevin Healy.
2000: Academy Awards
The actress liked this strapless Armani dress with a structured neckline so much, she rewore it on multiple occasions.
2000: Golden Globe Awards
Ryder attended the 57th annual Golden Globes wearing an embellished, white v-neck dress, on the arm of her then-boyfriend, Matt Damon.
1998: Smoke Signals Premiere
Another rare sighting of Ryder in color, the actress wore a knee-length, pale blue dress with a boatneck to the premiere of Smoke Signals in 1998.
1998: Vanity Fair Oscar Party
At the 1998 Vanity Fair Oscar party, Ryder arrived in a sleeveless black embellished dress with a matching shawl.
1997: Alien: Resurrection Premiere
Ryder kept things simple at the premiere of Alien: Resurrection, pairing a short-sleeve, ribbed turtleneck top with a leather knee-length skirt.
1997: Academy Awards
The actress wore a gothic vintage dress covered in beaded embellishments to the Oscars in 1997.
1996: Academy Awards
Ryder complimented this beaded Badgley Mischka dress with retro fingerwaves and a shawl.
1994: Little Women Premiere
The actress wore a velvet blazer a top a black dress to the premiere for the 1994 film, Little Women. She walked the red carpet with her then boyfriend, frontman of Soul Asylum Dave Pirner.
1994: Golden Globe Awards
Ryder wore a sleeveless, black column dress when she took her brother, Uri Horowitz, to the Golden Globes in 1994.
1993: The Age of Innocence Premiere
Wearing a deep purple, velvet sleeveless dress, Ryder attended the premiere of Age of Innocence with Pirner.
1992: Dracula Premiere
One of Ryder’s most unique looks to date, the actress wore a blue, corseted suit set lined with white lace to the premiere of Dracula in 1992.
1991: Little Man Tate Premiere
Ryder’s brown oversized suit would easily be in style today, over thirty years after she wore it to the Little Man Tate premiere in 1991.
1991: Golden Globe Awards
The actress wore a simple black wrap dress when she attended the Golden Globes with her then-boyfriend, Johnny Depp.
1990: Edward Scissorhands Premiere
Ryder attended the premiere of Edward Scissorhands in a black, satin mini dress alongside her costar and then-boyfriend, Depp.
1990: Cry Baby Premiere
While Depp went bold in an oversized, mustard yellow suit, Ryder kept to her usually black dress, this one with sheer long sleeves.
1989: Great Balls of Fire Premiere
Ryder wore a form-fitting, white off-the-shoulder dress to the premiere of Great Balls of Fire in 1989.
1988: Golden Globe Awards
The actress went fairly casual at the 1988 Golden Globes, wearing a red skirt with a black top and cardigan to the event, which she attended with then-boyfriend Rob Lowe.
Source: W Magazine
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