Here we map out some of Ryder's career-defining looks in memory of the perennially-iconic star.

By Balthazar Malevolent


Winona Ryder is one of the coolest girls of the 90s, hands down — or at least one of the most mysterious ones. In her early career, Ryder distinguished herself from the rest of the 90's starlets with her predilection for portraying freaks, geeks and weirdos, while also displaying some majorly impressive acting skills in more traditional, dramatic positions. As a performer, she masterfully inhabits the middle ground between horror movie icon and acclaimed lead actress, acting in roles as varied as the nihilistic, homicidal Veronica Sawyer of Beetlejuice's goth-y Lydia Deetz and Heathers to Little Women's brainy Jo March and socialite May Welland in Martin Scorsese's The Age of Innocence. At the height of her career — and perhaps inspired by her participation in the movie Girl, Interrupted — Winona was highly candid about her mental health problems, and unusual for an actress of her calibre. While some of these personal challenges and a highly scrutinized court case derailed her career briefly in the early 1900s, Winona re-emerged as "strange and odd" as she has ever been (and as we love her) starring in a new series of cult classics like Netflix's massively popular Stranger Things and tongue-in-cheek rom-com Destination Wedding alongside fellow 90s heartthrob (and partnering with her) Keanu Reeves. Here we map out some of Ryder's career-defining looks in memory of the perennially-iconic star.

Premiered at The Commitments, 1991

This dress, which Ryder wore to the 1991 musical comedy-drama The Commitments premiere, is for sure one of the most famous outfits of the nineties. You've probably seen this look several times, from Tumblr-era moodboards to your current Instagram feed. The combination of an old band T-shirt, lapelled leather jacket, and light-wash mom jeans are as timeless as they come — and timelessly covetable. Case in point: Winona continues to wear this Tom Waits T-shirt alongside Keanu Reeves to this day, last wearing it during the Destination Wedding in 2018.

Winona Ryder at The Commitments premiere in 1991.

Johnny Depp, 1990

Winona Ryder, with Edward Scissorhands co-star Johnny Depp, was one half of the hottest Hollywood couple of the 90s from the years 1989 to 1993. The pair had attracted huge media attention for both their A-lister status and strange reputations. Depp and Winona have been involved in her "first all" for three years, with Depp reportedly immortalizing the ink relationship. Depp changed his "Winona Forever" to "Wino Forever" following their break-up in 1993. Here, along with Johnny, Winona sports a leather jacket that is bulky and much worn. Although leather is par for the course when it comes to Winona 's wardrobe, the biker jacket looks as if it has been borrowed from Johnny.

Winona Ryder with Johnny Depp.

Beverly Hills Premiere at the Backdraft, 1991

Winona enjoyed a moment in power suit during the 90s. She was wearing a sumptuous brown suit for the 1991 premiere of Little Man Tate, this skirted number on a red carpet in the early 1990s, and who could forget her ridiculous 80s shouldering blazers like Veronica Sawyer in cult chic Heathers? Even after the 1990s, Winona is a major red carpet suiting arbiter, going as far as wearing a deconstructed blazer over a whole ballgown up to the SAG Awards in 2020. This version of the look, which she wore to the Backdraft premiere in 1991, stands out for its monochromatic palette and extreme late-80s proportions within the annals of Winona Ryder's many suits.

Winona Ryder at the Backdraft Beverly Hills premiere in 1991.

She attends the premiere of Dracula, 1992

Were you aware that Winona Ryder may actually have been married to Keanu Reeves, a fellow 90s heartthrob? Apparently, in Francis Ford Coppola's Dracula, the pair may have tied the knot for real during an extremely realistically staged wedding scene — officiated by a true Romanian priest. If this tidbit — shared for their rom-com Destination Wedding during Ryder and Reeves' press junket — is truth or fiction, it's clear that Ryder's Dracula premiere look is one of her iconicest. Combining the most iconic of the 80s (Heathers shoulders and square neckline) with that of the 90s (skirt suit and Manolo pumps), Ryder 's outfit diverged for a look as romantic as the film itself from her usual achromatic get-ups.

Winona Ryder attends the Dracula premiere in 1992.

In the fashion world, Rick Owens is known for his dark and revolutionary creations and is adored by many people who are gothic, surreal and expressive-inclined, including both Johnny Depp and Winona Ryder. If you're a fan of the fashion style of Rick Owens but don't know where to start, continue reading on our style inspirations to wear the trendy looks on the streets and make statements.

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