Pushing the confining boundaries of the Hollywood celeb beauty standards with her fair complexion, inky pixie cuts and kooky roles, Winona Ryder never wanted to fit the mould.
By Helena Madonna
Setting the tone for her career with her early roles as the moody adolescent type she became a black sheep in Hollywood and the poster girl for goths and outsiders. Challenging the hyper-feminine norms of the 90s by fulfilling roles with 'cautionary tale' charm or those best categorised under the 'weird girl' trope, she relished in and celebrated the notion of not fitting in.
Playing roles that centred some of the most iconic weirdly wonderful, cinematic worlds we've come to know and love; an angsty teen with an urge to dull her cookie-cutter existence in Edward Scissorhands neon suburbia, an alienated goth with ghostly friends in Beetlejuice's haunted playland, a high school student navigating her way through Heathers social hierarchy.
Time and time again she's provided a relatable element to every film she's starred in. Her iconic roles and timeless style have shaped her to be a true artefact of pop culture. Johnny Depp may have put it best in the old inky words he once had on his arm, Winona Forever.
1985
A young, fresh-faced, pre-fame Winona.
1986
A 14-year-old Winona in her film debut Lucas, also debuting her soon-to-be famous and iconic jet black
pixie cut.
1988
Lydia Deetz's fabulously dishevelled beehive and punk-flavoured split bang takes her Beetlejuice look to the next gothic level.
Winona's look in '89 cult classic Heathers. Obnoxious volume and fluffed to perfection, a look fitting for the exploration of high school cliques, social politics, oh and a touch of murder.
1989
The ultimate embodiment of iconic 80's hair.
1989
Casual yet elegant, photographed by Annie Leibovitz.
An unfinished science experiment with scissors for hands and his high school, sandy-haired sweetheart.
A bouncy, curly 'bixie' cut on 19 year old Winona for Movieline cover in 1990.
1990
A pic oozing with fabulousness from top to bathtub, featuring a neurotic Winona, glam bohemian mermaid Cher and baby Christina Ricci.
The mesh gowned Winona alongside mustard suited Johnny in 1990, forever our couples outfit inspo.
1991
Glossy natural curls and a deepened hue to tie together her got-to-gothy grungy early 90's look.
1992
Winona in her moody, vampy era for Francis Ford Coppola's Bram Stoker's Dracula.
1993
An innocent and polite Winona Ryder plays 1870's New York Society female ideal, May Welland in Martin Scorsese's The Age of Innocence.
Winona confronts the hard truths of life and love in Ben Stiller's Reality Bites.
A post shower, cosy and relaxed Winona for Rolling Stone in 1994
1996
Our queen alongside Daniel Day-Lewis in the witchy period piece, The Crucible, excels in highlighting how much it sucked to be a woman in the olden days.
A spiky-haired, verging on witchy Winona for '96's historical drama The Crucible.
1996
Winona sporting her classic duo, all black outfit with a pixie cut, at a Giorgio Armani party with Giorgio
Armani
1997
Alien: Resurrection premiere
'Off-duty model' cool for the MTV Video Music Awards, 1998.
A chic Winona in her simple silhouetted, sequined, showstopper gown for the '98 Vanity Fair Oscar
Party.
Girl Interrupted had our 2014 Tumblr feeds clogged with endless grungy outfit and hair inspo.
A chic, simple, underrated hair accessory, elevated by Winona's 2000's red carpet Armani look.
2001
Defining the 2024 trend, "Old Money Bob" in Friends episode 'The One with Rachel's Big Kiss'.
2010
A hot mess, mascara smudged, riddled with envy Winona acting on a dangerous impulse in ballet horror, Black Swan. Hair looks fab though.
Catwoman-esch, fierce and poised for Interview Magazine in 2013.
2016
A textured shag with feathered bangs, on-trend for both the '80s and our Tik Tok feeds.
2024
And Lydia Deetz is back! Winona Ryder alongside Jenna Ortega, Catherine Ohara and Justin Theroux for Beetlejuice Beetlejuice.
