Winona Ryder’s Best Red Carpet Moments, From 'Heathers' to 'Beetlejuice'

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.

Ryder wore a form-fitting, white off-the-shoulder dress to the premiere of Great Balls of Fire in 1989.

While Johnny Depp went bold in an oversized, mustard yellow suit, Ryder kept to her usually black dress, this one with sheer long sleeves.

Ryder attended the premiere of Edward Scissorhands in a black, satin mini dress alongside her costar and then-boyfriend, Depp.

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.

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.

Wearing a deep purple, velvet sleeveless dress, Ryder attended the premiere of Age of Innocence with her then boyfriend, frontman of Soul Asylum Dave Pirner.

Ryder wore a sleeveless, black column dress when she took her brother, Uri Horowitz, to the Golden Globes in 1994.

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 Pirner.

Ryder complimented this beaded Badgley Mischka dress with retro finger-waves and a shawl.

The actress wore a gothic vintage dress covered in beaded embellishments to the Oscars in 1997.

Ryder kept things simple at the premiere of Alien: Resurrection, pairing a short-sleeve, ribbed turtleneck top with a leather knee-length skirt.

At the 1998 Vanity Fair Oscar party, Ryder arrived in a sleeveless black embellished dress with a matching shawl.

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.

Ryder attended the 57th annual Golden Globes wearing an embellished, white v-neck dress, on the arm of her then-boyfriend, Matt Damon.

The actress liked this strapless Armani dress with a structured neckline so much, she rewore it on multiple occasions.

Ryder wore a greenish-gold strapless dress covered in embellishments to the Oscars in 2001, which she attended with her date, Kevin Healy.

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.

Wearing a mid-length, black dress with a black shawl, Ryder attended the Vanity Fair Oscar party with then-boyfriend, filmmaker Henry Alex-Rubin.

Ryder attended the 2007 Met Gala on the arm of Marc Jacobs, so it’s only fitting she wore a dress by the designer.

The actress wore an off-the-shoulder LBD to “The Model as Muse: Embodying Fashion” Costume Institute Gala in 2009.

What’s more fitting than wearing a dress with a tulle skirt to a premiere for a film about ballet?

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.

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.

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.

Ryder loves to pair a blazer with a dress, which is what she did at the premiere of Stranger Things back in 2016.

The actress brought a touch more glamour to the Golden Globes in 2017, wearing a strapless Viktor & Rolf dress on the red carpet.

Wearing an empire-waist gown with a bow detail, Ryder attended the season two premiere of Stranger Things.

Ryder wore a Ryan Roche black lace gown with a large heart pendant to the 2017 SAG Awards.

Ryder paired a black, floor-length dress with a blazer and satin clutch at the 24th annual SAG Awards.

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.

Ryder merged suit tailoring with feminine tulle in this Christian Dior spring 2018 haute couture dress at the 2020 SAG Awards.

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.

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.

Ryder stepped out in style for her first red carpet appearance in over two years. She wore a high-neck black coat from Elena Dawson that featured white buttons down the front for a Beetlejuice Beetlejuice photo call.