17 Throwback Pictures Of Winona Ryder You Probably Haven’t Seen Before

100% brave, brilliant and game-changing

Winona Ryder

by Lucy Morris |
Updated on

Winona Ryder is so much more than Joyce in Stranger Things. In the late ‘80s when Thatcher was in power, grunge was gaining momentum and chiselled Johnny Depp was everyone's bedroom-wall poster boy, Winona appeared on the scene. With alabaster skin, raven hair and the ability to make something as banal as jeans and a t-shirt look achingly-cool - she stood out.

Undoubtedly, this was helped by the fact she kept picking cult roles like the macabre goth Lydia Deetz in Beetlejuice, gun-wielding shoulder-pad lover Veronica Sawyer in Heathers and the pixie-haired normcore-originator Susanna in Girl, Interrupted.

Her red carpet appearances were a one-woman campaign in minimalism. Her hair was the antidote to the bouffant of the bronzed blonde foils the Hollywood machine kept spitting out. With Ryder firmly back in the public eye, and our hearts, let's take a walk through memory lane and remind ourselves just how she helped define the meaning of cool.

Winona Ryder SAG awards

Winona Ryder Looks That Must Us Want To Go Shopping, Now:


Iconic Winona Ryder Looks

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1. Prom Queen

Currently Googling 'Where can we get pink laces for Dr. Martens', wonder why…

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2. Fashion Habit

Her turn as a Catholicism-obsessed Jewish girl in 1990 flick Mermaids kickstarted our love affair (and maybe Alexa Chung's too?) with pleated skirts, Peter Pan collars and headbands.

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3. Icon Status

Name a more iconic Winona? With her a tad-too-big mom jeans, band tee and leather blazer, her raven hair and red lips, it's really no wonder she became the face of Gen-X.

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4. Jean Genie

On the surface, this is just mom jeans and a hoodie, but anyone with eyes can see that it's the boots that lift this look to another plane.

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5. Winona And Jim Jarmusch

Tell me what's more covetable: Winona's leather jacket or her shy independent filmmaker sidekick?

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6. Souped Up Vintage

Never flummoxed by the dress code, Ryder took the Academy Awards in 1997 in her stride with a thrifted beaded gown.

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7. Lessons On How To Wear Head-To-Toe White Without Looking Like A Bride

With her quintessential slick of coral lipstick, Winona elevates this sequined dress to new dimensions

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8. Beat This

Strange, alluring and deeply disturbing, Girl, Interrupted (which also starred Angelina Jolie) proved Winona could pull off the Beatnik look just as well as Allen Ginsberg, if not better.

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9. Pale And Interesting

Winona knows when to bank on her porcelain complexion to create drama with a dress.

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10. Red Star

Adding an element of grunge to her Eurythmic's band tee, Winona styled her ensemble with a bike chain necklace and choker. Instant cool.

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11. The Powers Of A Black Dress

Now, this is how you make minimalism show-stopping.

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12. Rose-Tinted

There are two things you rarely ever see Winona wear: pattern and colour. In this one-off sighting, the star proved she could give head-to-toe pink a beautiful spin. How? She relied on her old-friend minimalism.

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13. Band-Aid

Before Monica Rose could dilute the meaning of band tees, Winona wore them like a uniform.

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14. The Dark Haired Mia Farrow

Like Mia Farrow's iconic pixie, Winona's boyish cut became an icon in its own right.

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15. Flower Girl

Goals: Make men in badly fitted suits look out-of-place with a protest pin and a flower in your hair.

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16. Blazing Glory

Dark smokey eyes and slick monotoned tailoring, this is Winona's USP.

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17. Plastic Fantastic

It's the unexpectedness of her perspex heels that makes this all-black ensemble modern.

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