While Winona Ryder's style has almost always been rooted in 1990s fashion, she has certainly refined her look over the decades.
Leather biker jackets, baggy jeans, band T-shirts, oversized blazers and an abundance of black are some of the threads that held the twice Oscar-nominated actress's sartorial choices together as she rode a wave to fame following the success of 80s hits such as Beetlejuice and Heathers.
The gothic queen, who has grunge stylings down pat, first padded down red carpets in flats and baseball caps or slip dresses and chokers, particularly in the years she was in a relationship with Johnny Depp.
While her style hasn't evolved too far beyond dark, neutral hues, it has been modernised and refined.
Scroll through the gallery above to see how Winona Ryder's style has evolved through the decades.
The Stranger Things star has always had a clear sense of self in her style and was revisiting red carpet looks long before Emma Stone and Victoria Beckham entered the scene.
One fitted Armani column dress — black, of course — with a unique, dipping neckline was so beloved by Ryder she wore it to several high-profile events, including one in honour of Martin Scorsese in 1996, later that year while hanging out with pal Claire Danes at a cancer benefit, and four years later at the 72nd annual Academy Awards, the biggest event in Hollywood.
She's choosy about the brands she promotes, however, having fronted adverts for few labels, including Marc Jacobs, Rag & Bone and H&M.
Ryder's 90s stylings may have fallen out of favour in the noughties, but they have enjoyed revivals since then, such is the cyclical nature of fashion.
“There were certain things that were simply welcome — like, suddenly it was ‘cool’ to wear thrift store clothes, flannels, etc,” Ryder told Harpers Bazaar in 2018, speaking about the pros of style from that era.
“That was great in the sense that it was something that everyone could afford. I thought that was really cool. Then designers started making $500 flannel shirts and we were like, 'huh?'”
Black is undoubtedly the Girl, Interrupted star's shade of choice to this day, but she's also peppered in some colour from time to time. She famously donned a rather romantic cornflower blue button-down top and matching skirt with white, lacy edging to the Dracula premiere in 1992.
Another beloved look came in 1994, when she wore an off-white beaded dress with flapper-style fringe and a shawl with matching heels.
In the early 2000s, when Ryder was in court accused of shoplifting (she was found guilty), her '50s-inspired, well-put-together, feminine outfits that couldn't be less grunge became so talked-about that Robin Givhan quipped in a Washington Post thinkpiece: “She may be a shoplifter, but she has impeccable taste.”
For her latest red-carpet outings, however, particularly with Stranger Things, in which she plays mum Joyce Byers, she's stuck almost exclusively to black, albeit stylishly so, sporting brands such as Christian Dior, proving hers is a timeless style.
47 photos that chart Jennifer Aniston's style evolution — in pictures
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Actress Jennifer Aniston. Click through to see her style evolution. Getty Images -
Jennifer Aniston, in a denim waistcoat, poses for a promotional poster for TV show 'The Edge' in 1992. Getty Images -
Jennifer Aniston, with her famous bob, poses for a promotional poster for the television series 'Friends' in 1995. Getty Images -
Jennifer Aniston, in a satin LBD, and Lisa Kudrow at a Friends Helping Friends party in Beverly Hills, California, on September 22, 1997. Getty Images -
Lisa Kudrow, Courteney Cox and Jennifer Aniston, in a beaded black gown, at the annual Fire and Ice Ball in Hollywood, California, on March 12, 1997. Getty Images -
Matthew Perry and Jennifer Aniston, with a leopard print bag, at the premiere of 'Kissing a Fool' in Westwood, California, on February 18, 1998. Getty Images -
Jennifer Aniston, in mauve jersey, attends the VH1 Divas Live Concert in New York City, US, on April 18, 1998. Getty Images -
Jennifer Aniston, in a handkerchief top and maxi skirt, and Courteney Cox attend the annual Screen Actors Guild Awards at the Shrine Auditorium, in Los Angeles, California, on March 7, 1999. Getty Images -
Brad Pitt and Jennifer Aniston, in Randolph Duke, attend the 51st annual primetime Emmy Awards in Los Angeles, California, on September 12, 1999. Getty Images -
Jennifer Aniston, in a ribbed maxi dress, attends the Screen Actors Guild Awards in Beverly Hills, California, on March 12, 2000. Getty Images -
Brad Pitt and Jennifer Aniston, in Prada, arrive at the 52nd annual Primetime Emmy Awards on September 10, 2000 in Los Angeles, California. Getty Images -
Courteney Cox, Lisa Kudrow and Jennifer Aniston, in a spaghetti-strapped gown, attend the Fire and Ice Ball at the Beverly Hilton Hotel in Los Angeles, California, on November 12, 2000. Getty Images -
Jennifer Aniston, in a silky black dress, and David Schwimmer arrive at the 27th annual People's Choice Awards at the Pasadena Civic Auditorium in Los Angeles, California, on January 7, 2001. Getty Images -
Brad Pitt and Jennifer Aniston, in a cream jacket and matching trousers, arrive for the premiere of 'The Mexican' on February 23, 2001 in Westwood, California. Getty Images -
Jennifer Aniston, in a strapless red dress with a black coat, arrives at the premiere of 'Along Came Polly' at the Empire Leicester Square on February 18, 2004 in London, England. Getty Images -
Brad Pitt and Jennifer Aniston, in Versace, attend the premiere of 'Troy' at Le Palais de Festival on May 13, 2004 in Cannes, France. Getty Images -
Jennifer Aniston, in Chanel, arrives for the 56th annual Primetime Emmy Awards at the Shrine Auditorium in Los Angeles, on September 19, 2004. EPA -
Jennifer Aniston, in Rochas, attends the 78th annual Academy Awards in Hollywood, California, on March 5, 2006. EPA -
Jennifer Aniston, in a silver slip dress, attends a screening of 'The Break-Up' on June 12, 2006 in Hamburg, Germany. Getty Images -
Jennifer Aniston, in a charcoal mini, arrives at the premiere of 'The Break-Up' at the Vue West End on June 14, 2006 in London, England. Getty Images -
Jennifer Aniston, in Burberry, attends the premiere of 'Marley And Me' at the Vue West End on March 2, 2009 in London, England. Getty Images -
Jennifer Aniston, in Prada, attends the Women in Film Awards at the Hyatt Regency Century Plaza in Los Angeles, California, on June 12, 2009. EPA -
Jennifer Aniston, in Celine, attends the Mamounia hotel launch party on November 26, 2009 in Marrakech, Morocco. Getty Images -
Jennifer Aniston, in Valentino, attends the premiere of 'The Bounty Hunter' at Vue West End on March 11, 2010 in London, England. Getty Images -
Jennifer Aniston, in Christian Lacroix, attends the premiere of 'The Bounty Hunter' at Cinema Gaumont Marignan on March 28, 2010 in Paris, France. Getty Images -
Jennifer Aniston, in Valentino, attends 'The Bounty Hunter' premiere at the Callao cinema on March 30, 2010 in Madrid, Spain. Getty Images -
Jennifer Aniston, in Nina Ricci, attends the 'Just Go With It' premiere at CineStar on February 21, 2011 in Berlin, Germany. Getty Images -
Jennifer Aniston, in Valentino, attends the premiere of 'Horrible Bosses' at BFI Southbank on July 20, 2011 in London, England. Getty Images -
Jennifer Aniston, in Valentino, attends the 85th Academy Awards at the Dolby Theatre in Hollywood, California, on February 24, 2013. EPA -
Jennifer Aniston, in Dior, attends the premiere of 'We're The Millers' at Odeon West End on August 14, 2013 in London, England. Getty Images -
Jennifer Aniston, in Alexander McQueen, arrives for the premiere of 'We're the Millers' at Cinestar in Potsdamer Square in Berlin, Germany, on August 15, 2013. EPA -
Jennifer Aniston, in Vivienne Westwood, arrives for the screening of 'Life of Crime' during the 38th annual Toronto Film Festival, in Toronto, Canada, on September 14, 2013. EPA -
Jennifer Aniston, in Antonio Berardi, attends the premiere of 'Horrible Bosses 2' at Odeon West End on November 12, 2014 in London, England. Getty Images -
Jennifer Aniston, in Bouchra Jarrar, attends the 'Horrible Bosses 2' photocall at Corinthia Hotel London on November 13, 2014 in London, England. Getty Images -
Jennifer Aniston, in Saint Laurent, arrives for the 72nd annual Golden Globe Awards at the Beverly Hilton Hotel in Beverly Hills, California, on January 11, 2015. EPA -
Jennifer Aniston, in Gucci, arrives for the 20th annual Critics' Choice Awards in Hollywood, California, on January 15, 2015. EPA -
Jennifer Aniston, in Galliano, arrives at the 21st annual Screen Actors Guild Awards at the Shrine Auditorium in Los Angeles, California, on January 25, 2015. EPA -
Jennifer Aniston, in Versace, arrives for the 87th annual Academy Awards at the Dolby Theatre in Hollywood, California, on February 22, 2015. EPA -
Jennifer Aniston, in Saint Laurent, and Justin Theroux arrive for the 21st annual Critics' Choice Awards at Barker Hangar in Santa Monica, California, on January 17, 2016. EPA -
Jennifer Aniston, in Tibi, attends the Giffoni Film Festival on July 23, 2016 in Giffoni Valle Piana, Italy. Getty Images -
Jennifer Aniston, in Valentino, arrives for the premiere of 'Storks' at the Regency Village Theatre in Westwood, Los Angeles, California, on September 17, 2016. EPA -
Jennifer Aniston, in Roberto Cavalli, arrives for the premiere of 'Office Christmas Party' at the Regency Village Theatre in Westwood, California, on December 7, 2016. EPA -
Jennifer Aniston, in Versace, arrives for the Vanity Fair Oscar Party following the 89th annual Academy Awards in Beverly Hills, California, on February 26, 2017. EPA -
Jennifer Aniston, in Christian Lacroix , arrives for the American Film Institute Life Achievement Award Gala at The Dolby Theatre in Hollywood, California, on June 7, 2018. EPA -
Jennifer Aniston, in Louis Vuitton, and Justin Theroux attend a Louis Vuitton launch party at the Louvre Museum in Paris, France, on April 11, 2017. EPA -
Jennifer Aniston, in Stella McCartney, arrives for the premiere of 'Dumplin' at the TCL Chinese 6 Theatre in Hollywood, California, on December 6, 2018. EPA -
Jennifer Aniston, in Dior, arrives for the 77th annual Golden Globe Awards at the Beverly Hilton Hotel in Beverly Hills, California, on January 5, 2020. EPA -
Jennifer Aniston, in Dior, arrives for the 26th annual Screen Actors Guild Awards at the Shrine Auditorium in Los Angeles, California, on January 19, 2020. EPA
