A look back at Winona Ryder's fashion evolution: How the 'little black dress' became her favourite
Beetlejuice, Heathers, Edward Scissorhands and Stranger Things.
These are just some of the roles that put – and kept – Winona Ryder's name up in lights.
The actress has been an icon of the big screen since the '80s, and still is today.
While she's most recognised for her acting talents, the Hollywood legend has long been a leading lady in the fashion game.
The star's style in the '80s and '90s had everything from casual chic street style to glamorous gowns for awards season.
Over the years, however, there's been one clear standout in Ryder's wardrobe...
Enter: the little black dress!
Ryder has worn the iconic LBD fashion staple in every way you can imagine over the years – including a preppy take on the trend for her recent Venice Film Festival outing.
Scroll on to see how the star became the queen of the little black dress.
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1989
This photo was taken just a year after Winona Ryder – aged 18 in the picture – shot to fame as Lydia Deetz in the Tim Burton horror comedy Beetlejuice (1988).
"I completely identified with it," Ryder told Vogue in 2024 about the Burton film.
"They didn't have to do much to me to make me look the way that I did," she said, drawing comparisons between her own style and that of her gothic teen character Lydia.
In the same year as Beetlejuice, Ryder starred in another one of her biggest career hits – Heathers.
Here the star is pictured at the Damien Elwes' Art Exhibtion on April 29, 1989 in Hollywood wearing a leather jacket and denim skirt over sheer black stockings.
1991
Back in her early career when she was dating Johnny Depp, Ryder made a glamorous appearance with the actor at the 48th annual Golden Globe Awards.
Ryder wore a low-cut mini dress for the evening with a black bow at her waist.
While the star had iconic choppy micro bangs for and around the time of Beetlejuice, by the early '90s she was rocking a chic bouncy bob haircut.
1991
She's always loved to wear black!
Ryder opted for a monochromatic look for The Silence of the Lambs premiere in 1991.
The star paired her look with a subtle coloured lip and understated makeup.
As pictured, the actress walked hand-in-hand with then-boyfriend Depp as she arrived for the premiere in Century City, California.
1991
One of her most memorable street style moments happened to be a look thrown together using some of Ryder's cherished pieces from her own wardrobe.
In August 1991 the actress was pictured attending The Commitments premiere in Hollywood wearing a pair of belted cuff jeans, a band shirt and leather jacket.
Breaking down the look to Vogue in September, Ryder said it had been put together after a last-minute invite.
"I was wearing my old Doc Martens, my precious Tom Waits T-shirt that I wear all of the time, and a leather jacket that was my mum's," she said.
1992
For the 1992 Dracula premiere in Hollywood, Ryder arrived at the Mann's Chinese Theatre wearing a beautiful blue corset jacket and matching skirt with striking lace details.
The star still had her hair dyed black and styled in a chin-length bob at this point.
1994
Winona Ryder might have made her first Oscars appearance in 1989 with then-boyfriend Christian Slater, but it was the 1994 Academy Awards that saw her score her first nomination.
Ryder was nominated in the best supporting actress category for her role in the 1993 film The Age of Innocence.
The star wore this gorgeous 1920s-esque sparkly flapper gown for the milestone.
By this time, she'd also said goodbye to the 'bob' and debuted a bold new pixie cut.
Ryder spoke about the iconic gown with Vogue, revealing one part of her look left her a bit concerned.
The star said she was "nervous about sitting and not breaking the beads."
"I was just trying to take care of the beads," the said with a laugh.
1996
Winona Ryder has always known how to dress for a glamorous occasion in Hollywood – just look here at her 1996 Academy Awards appearance.
By this time, Ryder had gained notoriety for her roles in Edward Scissorhands and as Jo March in the 1994 adaptation of Little Women.
For the 68th annual Academy Awards, Ryder wore a gorgeous Badgley Mischka gown – not dissimilar to her glitzy 1994 Oscars dress, but with a sheer shawl.
Winona Ryder
After many big credits to her name, Winona Ryder received a star on the Hollywood Walk of Fame in 2000.
For her big moment, Ryder wore another sparkling gown that looked incredibly similar to her dress from the 1996 Academy Awards just four years earlier.
Ryder paired her look with a silky shawl and gorgeous patterned mini purse.
The star was wearing her hair longer and in layers by the early noughties. She had also swapped her signature black colour for a dark blonde.
2006
Ryder had worn black dresses throughout the '90s, but the garment – worn in every style under the sun – became an even more frequent red carpet choice.
Just look at this gorgeous A-line frock the actress wore to the Vanity Fair Oscar Party in West Hollywood in 2006.
Ryder looked straight out of the '50s with this dress and matching black heels.
