29 October 2021

Winona Ryder turns 50: The iconic actor’s fashion and beauty evolution

29 October 2021

Making her big screen debut when she was still a teenager, Winona Ryder has been in the showbiz spotlight since the mid-80s, her impressive career spanning five decades and featuring some unforgettable roles.

Not only is she an award-winning actor, Ryder, who turns 50 on October 29, is a fashion and beauty icon too, thanks to her impeccable outfits and lust-worthy haircuts.

To mark her milestone birthday, we look back at how Winona Ryder’s style – both on and off the screen – has evolved throughout the decades.

90s ingénue

Winona Ryder attends ‘The Commitments’ Hollywood Premiere in 1991 (Alamy/PA)

Named after her hometown, Winona Laura Horowitz was born in Winona, Minnesota in 1971.

After taking acting classes and adopting the stage name Winona Ryder, the 15-year-old made her film debut in Lucas (1986) which was quickly followed by her breakout role as Lydia Deetz in Tim Burton’s Beetlejuice, for which Ryder’s hair was dyed jet black.

Parts in several other cult classics soon followed. In high school satire, Heathers, she donned 80s jackets with huge shoulder pads and had voluminous hair to match.

Playing Kim in Edward Scissorhands (Alamy/PA)

Ryder was reunited with Tim Burton for 1990’s Edward Scissorhands, this time given long, blonde locks and a prim and proper wardrobe to star opposite Johnny Depp.

Gothic glamour

Johnny Depp and Winona Ryder at the 1996 Golden Globe Awards (Alamy/PA)

Ryder and Depp started dating and became one of the most famous Hollywood couples of the time.

Depp declared that he was madly in love with his Edward Scissorhands co-star and even got ‘Winona Forever’ tattooed on his arm. Sadly, the pair split after four years and Depp chose to change his tattoo to read ‘Wino Forever’.

Attending an event to celebrate Martin Scorsese in 1996 Alamy/PA)

By then a regular on the red carpet, Ryder was all about understated glamour in her 20s, often seen in sweeping black dresses with slicked back hair and a red lip.

At the 1994 Academy Awards (Alamy/PA)

Occasionally she would mix it up with a pink, red or cream column dress, but there was always something timeless about Ryder’s red carpet style.

Pretty as a pixie

Starring in Alien Resurrection (Alamy/PA)

In 1997, Ryder debuted a dramatic hair transformation with the short pixie crop first seen on screen in Alien Resurrection.


The artfully messy ‘do perfectly suited Ryder’s elfin features and has gone down as one of the most covetable celebrity pixie cuts in history.

Noughties revamp

Ryder at the 2001 Vanity Fair Oscars Party (Alamy/PA)

Within a few years the pixie was gone, replaced by honey-blonde tousled locks.

In 2001, Ryder hit the headlines when she was caught shoplifting in Beverly Hills and sentenced to three years probation.

At the premier of Before Sunset in 2004 (Alamy/PA)

After disappearing from the spotlight for some time, Ryder was back on the red carpet by 2004 with a boho-chic new look and her wavy, shoulder-length locks back to brunette.

The return of the pixie

At the Milk premiere in 2008 (Alamy/PA)

In 2008, the pixie crop returned – this time a longer, softer style with a glossy, chocolate brown hue – and Ryder’s career began to take off again, with supporting roles in films such as Star Trek and Black Swan.

Grown-up glam

Attending the Black Swan press conference at the Toronto Film Festival 2010 (Alamy/PA)

As Ryder headed into her 40s, her style continued to evolve. She embraced tomboyish tailored looks as well as show-stopping gowns like the Alberta Ferretti number at the 2011 SAG Awards.

On the SAG Awards red carpet (Alamy/PA)

Stranger Things star

Winona Ryder and Noah Schnapp at the Netflix’s season 2 premiere of Stranger Things (Alamy/PA)

Enjoying something of a renaissance in the last few years, Ryder was cast as Joyce Byers in critically-acclaimed Netflix series Stranger Things in 2016.

The hit series has introduced the actor to a whole new generation, and she’s set to reprise her role in season four next year.

On the 2017 Golden Globes red carpet (Alamy/PA)

Off-screen, Ryder continues to rock the gothic glam look with a seemingly endless supply of glitzy black gowns.

Clearly, the actor has found her fashion groove, and she looks as stylish at 50 as she did when she was starting out in showbiz.

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