Winona Ryder’s definitive style moments

There is something about Winona Ryder that is hard to shake off. On the line between delicate girlishness and unapologetic grunge, her charm and nonchalant style inspired the most iconic cult looks of the 90s. After a relatively quiet few years on the fashion front, the actress has recently been announced as the next star to feature in Marc Jacobs’ AW15 campaign – shot against a striking red background by David Sims and styled by Katie Grand, she joins the likes of Willow Smith, Cher and Molly Bair. In light of the return of the Jacobs-Ryder collaboration, here’s Dazed's list of star’s best style moments (and her most iconic roles).

TEENAGE YEARS

While she was bullied as a teen for “looking like a boy” and even kicked out of school after getting beaten up, the actress rocked spiked up short hair (inspired by Bugsy Malone, she says), baggy clothes, and beaded necklaces. Years later, she bumped into one of her bullies and ended up having the last word (as if being Winona Ryder wasn’t enough).“I went to a coffee shop and I ran into one of the girls who'd kicked me, and she said, 'Winona, Winona, can I have your autograph?' And I said, 'Do you remember me? Remember in seventh grade you beat up that kid?' And she said, 'Kind of'. And I said, 'That was me. Go fuck yourself.'” You tell ’em, girl. 

VERONICA SAWYER IN HEATHERS (1988)

Ryder made cult history as Veronica Sawyer in 1988 classic, Heathers. The actress played a privileged girl who loathes the popular clique at high school – despite being in it. Between drinking slushies and forging letters of teenage suicide alongside Christian Slater’s charming, and yet completely insane JD – she rocked the blowout hairstyle, standing out amongst her power suit wearing, cricket playing “friends” in a grey cardigan worn over a high-waisted skirt and topped off with a signature cigarette.

LYDIA DEETZ IN BEETLEJUICE (1988)

Decked out in all-black, loose-fitting clothes with a fringe to die for, Lydia lived her life surrounded by film cameras and ghouls, leaving every teen goth fuming with envy and aspiration. In Tim Burton’s Beetlejuice, Ryder wore everything that mattered – from the widest brimmed hat to her blood-red wedding gown, which really complemented her intended’s striped suit. She left us all wanting to find a handbook for the recently deceased – just so we could emulate that wardrobe.

CHARLOTTE FLAX IN MERMAIDS (1990)

Rocking the kinderwhore style – complete with a Peter Pan collar and loose boots – Winona starred as a Jewish girl obsessed with Catholicism in 1990 flick, Mermaids. She played the remarkable character Charlotte Flax, in an honest and compelling coming of age story. It’s hard to compete with Cher for attention (she played Ryder’s mother in the film), but Ryder’s role as the teenage narrator figuring out family, sexuality and expectations earned her a Golden Globe nomination for best supporting actress.

ON THE RED CARPET WITH JOHNNY DEPP

Johnny Depp and Winona Ryder were the ultimate cult 90s couple, having one of the most-loved romances of the decade. Often in rock ’n' roll ensembles of head-to-toe black, they lit up every red carpet – and always looked absolutely enthralled by each others’ presence. Style highlights whilst she was dating Depp were her tight-fitting velvet dresses combined with oversized coats and borrowed from the boys blazers.

KIM BOGGS IN EDWARD SCISSORHANDS (1990)

Starring in another Tim Burton film, Ryder played Kim Boggs – an ethereal girl born and raised in suburbia. She acted opposite Johnny Depp (who happened to be her boyfriend at the time), as the angelic girl-next-door. With her permed, blonde hair and puffy fringe and white dress, Ryder was the perfect counterpoint to Depp’s dark, gothic character.

SUSANNA KAYSEN IN GIRL, INTERRUPTED

After overdosing on aspirin to stop a headache, pixie-haired Susanna Kaysen is committed to a mental health institution. Whilst there, she befriends the ever-charming bleached-blonde sociopath Lisa Rowe, played by Angelina Jolie. Between dating Jared Leto and trying to figure life out, Susanna’s look is the epitome of the 60s beatnik girl. A free spirited writer, as the character herself wanted to be, in boat-necked striped shirts and close-cut cigarette trousers.

90s GRUNGE

In baggy denim trousers and black chokers, combined with that ever-present leather jacket that made oh-so-many red carpet appearances – Ryder’s nonchalant cool mixed her delicate demeanour with her gritty style. Appearing beside constantly disheveled looking boyfriend Dave Pirner (who she started dating after her break-up with Depp), she exuded an air of grunge-inspired confidence and fearless rebellion.

2003 MARC JACOBS CAMPAIGN

During her six day trial for shoplifting in 2002, Ryder sported head-to-toe Marc Jacobs. Fittingly, she appeared in her first campaign since the arrest, for the brand’s SS03 collection. Photographed by the designers’ long term collaborator Juergen Teller – she is shown with messy hair, lounging around in a hotel room. In one of the most iconic pictures from the campaign, a pair of scissors is shown beside the actress as she holds up a brand-new sweater – a clear tongue-in-cheek reference to the actress’ arrest, where she was charged for cutting the security tags off merchandise.

FOR MARC JACOBS AW15

Showing that her rep as a Marc Jacobs muse wasn’t just a fad, Ryder is back for AW15. Joining Cher, Willow Smith, Anthony Kiedis and his son Everly Bear, Ryder can be found posing against that now instantly recognisable red background. Jacobs had a very clear vision when it came to choosing his models: “Beauty, style and talent know no age. It is those individuals whose creativity, unique vision, and voice inspire all of us here to create and express ourselves through our medium: fashion.” Winona certainly fits the bill.