queen of timeless ’90s fashion and LBDs

While Winona Ryder’s style has almost always been rooted in 1990s fashion, she has certainly refined her look over the decades.

Leather biker jackets, baggy jeans, band T-shirts, oversized blazers and an abundance of black are some of the threads that held the twice Oscar-nominated actress’s sartorial choices together as she rode a wave to fame following the success of 80s hits such as Beetlejuice and Heathers.

The gothic queen, who has grunge stylings down pat, first padded down red carpets in flats and baseball caps or slip dresses and chokers, particularly in the years she was in a relationship with Johnny Depp.

While her style hasn’t evolved too far beyond dark, neutral hues, it has been modernised and refined.

Scroll through the gallery above to see how Winona Ryder’s style has evolved through the decades.

The Stranger Things star has always had a clear sense of self in her style and was revisiting red carpet looks long before Emma Stone and Victoria Beckham entered the scene.

One fitted Armani column dress — black, of course — with a unique, dipping neckline was so beloved by Ryder she wore it to several high-profile events, including one in honour of Martin Scorsese in 1996, later that year while hanging out with pal Claire Danes at a cancer benefit, and four years later at the 72nd annual Academy Awards, the biggest event in Hollywood.

She’s choosy about the brands she promotes, however, having fronted adverts for few labels, including Marc Jacobs, Rag & Bone and H&M.

Ryder’s 90s stylings may have fallen out of favour in the noughties, but they have enjoyed revivals since then, such is the cyclical nature of fashion.

“There were certain things that were simply welcome — like, suddenly it was ‘cool’ to wear thrift store clothes, flannels, etc,” Ryder told Harpers Bazaar in 2018, speaking about the pros of style from that era.

“That was great in the sense that it was something that everyone could afford. I thought that was really cool. Then designers started making $500 flannel shirts and we were like, ‘huh?’”

Black is undoubtedly the Girl, Interrupted star’s shade of choice to this day, but she’s also peppered in some colour from time to time. She famously donned a rather romantic cornflower blue button-down top and matching skirt with white, lacy edging to the Dracula premiere in 1992.

Winona Ryder attends 'Stranger Things' season 4 premiere at Netflix in Brooklyn, New York City on May 14, 2022. AFP

Another beloved look came in 1994, when she wore an off-white beaded dress with flapper-style fringe and a shawl with matching heels.

In the early 2000s, when Ryder was in court accused of shoplifting (she was found guilty), her ’50s-inspired, well-put-together, feminine outfits that couldn’t be less grunge became so talked-about that Robin Givhan quipped in a Washington Post thinkpiece: “She may be a shoplifter, but she has impeccable taste.”

For her latest red-carpet outings, however, particularly with Stranger Things, in which she plays mum Joyce Byers, she’s stuck almost exclusively to black, albeit stylishly so, sporting brands such as Christian Dior, proving hers is a timeless style.

Updated: May 31, 2022, 1:25 PM


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