Winona Ryder style evolution: queen of timeless '90s fashion and LBDs

The 'Stranger Things' star perhaps hasn't evolved as much as refined her look over the decades

Winona Ryder, wearing a grey jacket over a black jumper and shirt, with Michael Nesmith of The Monkees at the premiere of 'Amazing Grace and Chuck' on March 26, 1987. Getty

Rob Lowe with Winona Ryder, who wears a black blazer and red skirt, at the 45th Annual Golden Globe Awards on January 23, 1988. Getty

Winona Ryder in a blush pink long-sleeved shirt for an after-event party at 31st Grammy Awards on February 22, 1989. Getty

Winona Ryder, accompanied by Keanu Reeves, wears a fitted white top and matching skirt at the Fourth Annual Independent Spirit Awards on March 25, 1989, at the Hollywood Roosevelt Hotel in Hollywood, California. Getty

Winona Ryder, accompanied by Christian Slater, wears a classic strappy black dress at the Shrine Auditorium for the 61st Annual Academy Awards in Los Angeles, California on March 29, 1989. Getty

Winona Ryder in denim and leather at Damien Elwes' art exhibition at the CAZ Gallery in West Hollywood, California, on April 29, 1989. Getty

Winona Ryder, accompanied by Johnny Depp, wears a leather biker jacket to the 1990 Nato/ShoWest Convention on February 8, 1990 at Bally's Hotel and Casino in Las Vegas, Nevada. Getty

Winona Ryder, in a black dress with opaque sleeves, is joined by Johnny Depp at the 'Cry Baby' premiere on July 1, 1990. Getty

Winona Ryder, accompanied by Johnny Depp, in a little black dress at the 48th Annual Golden Globe Awards on January 19, 1991 at Beverly Hilton Hotel in Beverly Hills, California. Getty

Winona Ryder in a black suit and oversized blazer attends the 'Backdraft' Beverly Hills premiere on May 22, 1991 at the Academy Theatre. Getty

Winona Ryder in jeans, band T-shirt, biker jacket and boots, attends 'The Commitments' premiere on August 7, 1991 at Pacific's Cinerama Dome in Hollywood, California. Getty

Sadie Frost, Winona Ryder, in a cornflower button-down top and matching skirt, and Gary Oldman at the world premiere of Bram Stoker's 'Dracula' on November 10, 1992. Getty

Singer Dave Pirner of Soul Asylum and Winona Ryder, in a deep purple velvet dress attend 'The Age of Innocence' New York City premiere on September 13, 1993 at the Ziegfeld Theatre. Getty

Winona Ryder in a fitted off-white dress with flapper-style fringe at the 66th Academy Awards on March 21, 1994. Getty

Actress Winona Ryder, rewearing an Armani gown, and actress Claire Danes attend the Seventh Annual Fire & Ice Ball to Benefit Revlon/UCLA Women's Cancer Research Programme on January 17, 1996 at Warner Bros Studios in Burbank, California. Getty

Winona Ryder in a blush gown at the 68th Academy Awards on March 25, 1996. Getty

Winona Ryder in an A-line-style patterned dress at the American Movie Classics Presents Ladies Of The Musicals at Beverly Hills Hotel in California on June 12, 1996. Getty

Winona Ryder, in a strappy pink gown and shawl, attends the 25th Annual American Film Institute Lifetime Achievement Award Salute to Martin Scorsese on February 20, 1997 at Beverly Hilton Hotel in California. Getty

Winona Ryder wears a vintage beaded dress to the Vanity Fair Oscars party on March 24, 1997. Getty

Winona Ryder in an A-line dress at the American Movie Classics' Fifth Annual Film Preservation Festival - 'Salute to Film Noir' on September 25, 1997 at the El Rey Theatre in Los Angeles, California. Getty

Winona Ryder wearing black and leather at the premiere of 'Alien Resurrection' in Westwood, California, on November 20, 1997.

Winona Ryder in a blue, A-line, fitted dress at the New York premiere of 'Smoke Signals' on June 23, 1998. Reuters

Winona Ryder in black strappy top and leather skirt, enters the premiere of 'Girl, Interrupted' in Hollywood, California, on December 7, 1999. Online USA/Newsmakers

Winona Ryder in white arrives at the 57th annual Golden Globe Awards in Beverly Hills, California, on January 23, 2000. Reuters

Winona Ryder rewears her Armani gown at the 72nd Annual Academy Awards on March 26, 2000, in Los Angeles, California. Photo: David McNew

Winona Ryder in an off-white dress and soft shawl, on October 6, 2000, during a ceremony to unveil her star on the Hollywood Walk of Fame in Hollywood. Newsmakers

Winona Ryder in a black jacket with silver clutch at the premiere of 'Lost Souls' at the Egyptian Theatre in Los Angeles, California, on November 10, 2000. Getty

Winona Ryder in a denim jacket at the premiere of Warner Bros Pictures' 'The Pledge' on January 9, 2001 at the Egyptian Theatre in Hollywood, California. Liaison

Winona Ryder in printed black-and-white jacket with burgundy handbag at a handprint ceremony honouring actor Anthony Hopkins at the Famous Mann's Chinese Theatre on January 11, 2001, in Hollywood, California. Newsmakers

Winona Ryder wears a golden gown for the 73rd Annual Academy Awards March 25, 2001, at the Shrine Auditorium in Los Angeles. Getty

Winona Ryder in mauve at the British premiere of 'Planet Of The Apes' in London, England, on August 14, 2001. Getty

Winona Ryder in a deep red, off-the-shoulder gown, attends the American Museum Of The Moving Image Salute to Richard Gere at The Waldorf-Astoria Hotel on April 20, 2004, in New York City. AFP

Winona Ryder in a boho-inspired outfit with actor Ethan Hawke at the Los Angeles Film Festival Premiere of 'Before Sunset' at the Archlight Cinema on June 23, 2004. Getty

Winona Ryder wears grey to the block party in celebration of the opening of Marc Jacobs stores. Melrose Place, Los Angeles, California, March 17, 2005. AFP

Winona Ryder arrives at the 35th AFI Life Achievement Award tribute to Al Pacino in an A-line, strapless black dress at the Kodak Theatre on June 7, 2007 in Hollywood, California. AFP

Winona Ryder arrives at the Valentino Paris Fashion Week Autumn-Winter show on February 28, 2008, in Paris, France. Getty

Winona Ryder in a cream dress with black edging arrives at the Los Angeles premiere of Focus Features' 'Milk', held at the Academy of Motion Picture Arts and Sciences on November 13, 2008 in Beverly Hills, California. Getty

Winona Ryder in a blush, floor-length, strapless gown at the Marie Claire Prix de la Mode 2008 awards at French embassy in Madrid, Spain, on November 20, 2008. Getty

Winona Ryder in a Givenchy by Riccardo Tisci suit at the premiere of 'Black Swan' at the Ziegfeld Theatre in New York on November 30, 2010.

Winona Ryder wears an Alberta Ferretti bridal gown at the 17th Annual Screen Actors Guild Awards held at The Shrine Auditorium in Los Angeles, California, on January 30, 2011. Getty

Winona Ryder attends the Marni at H&M Collection launch at Lloyd Wrights Sowden House, in Los Angeles, California on February 17, 2012. Getty

Winona Ryder in a black Dolce & Gabbana gown at the 'The Iceman' premiere during the 69th Venice Film Festival at the Palazzo del Cinema on August 30, 2012. Getty

Winona Ryder walks the red carpet in a black dress with ruffled skirt and white collar at the premiere of Tim Burton's Frankenweenie at the Alamo Drafthouse in Austin, Texas, on September 20, 2012. FilmMagic

Winona Ryder in a little black dress and heels at the Las Vegas premiere of Open Road Films' 'Homefront' at Planet Hollywood Resort & Casino in Las Vegas, Nevada, on November 20, 2013. Getty

Winona Ryder in a black dress attends the premiere of 'Experimenter' during the 53rd New York Film Festival at Alice Tully Hall, Lincoln Centre on October 6, 2015. Getty

Winona Ryder in a strappy black dress attends the Marc Jacobs Spring 2016 fashion show during New York Fashion Week at Ziegfeld Theater on September 17, 2015. Getty

Winona Ryder, accompanied by fashion designer Scott Mackinlay Hahn, wears a custom Viktor & Rolf gown to the 74th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 8, 2017. Getty

Winona Ryder in a black dress for the season 3 premiere of 'Stranger Things' on June 28, 2019, in Santa Monica, California. AP

Winona Ryder, in Christian Dior, arrives for the 26th Annual Screen Actors Guild Awards at the Shrine Auditorium in Los Angeles, California, on January 19, 2020. AFP

Winona Ryder in a three-piece suit at the premiere of 'Stranger Things' season 4 at Netflix Studios Brooklyn on Saturday, May 14, 2022, in New York. AP

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.

Johnny Depp and Winona Ryder, in a little black dress, attend the 48th Annual Golden Globe Awards on January 19, 1991 at Beverly Hilton Hotel in Beverly Hills, California. Getty Images

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.

Winona Ryder attends 'Stranger Things' season 4 premiere at Netflix in Brooklyn, New York City on May 14, 2022. AFP

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

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