The 50 Most Unforgettable Fashion Moments

Liz Doupnik
The 50 Most Unforgettable Fashion Moments
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“The times they are a-changing,” words once sung by a budding folk singer by the name of Bob Dylan, seem not only applicable to the upheaval of values and barriers in the 1960s, but also an industry that thrives on reinvention. Even as we peer into our closets – no matter how frightening the state they may currently reside – we can see phases of our personality beaming in front of us like old friends saying hello.

So, as we approached the inevitable question of what to wear for the day, we checked off the different references and genres in our heads and hangers, which got us thinking. Whether we feel like channeling Twiggy in a mod swinging mini-dress or Sporty Spice in a pair of platform Converse, it’s all there: these major fashion moments.

From movies to mishaps, this industry rolls with the punches, doing it in a style that can only be accessorized and triumphed by some of the world’s most influential creatives. With that, we decided to search through our DVD collections, books and magazine archives to collect some of the most influential moments we’ve seen since the early 20th century.

Trust us, this memory lane is looking more and more like a runway that you won’t want to miss. Strut through the slideshow to see our 50 most memorable fashion moments, work it!

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Spice Girls... need we say more?

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Alexander McQueen shocked fashion's elite with a hologram called "The Ghost of Kate Moss."


Marilyn Monroe wearing her iconic white dress in the movie, Seven Year Itch.

J. Lo in Versace at the 2000 Grammy Awards.

Audrey Hepburn as Holly Golightly in Breakfast at Tiffany's.

Justin Timberlake and Britney Spears sporting matching denim patchwork at the 2001 American Music Awards.

Grace Kelly makes fashion history with her wedding dress.

Elizabeth Taylor in Cleopatra.

Bye-bye crew cuts, hello Beatles. The four mop tops shocked British airwaves with their new version of rock 'n' roll, super tailored trousers and shaggy 'dos.

Photo: Telegraph UK/

Lady Gaga wore a meat dress to the 2010 MTV Video Music Awards.

Keira Knightley graces us with this unforgettable green dress in Atonement.

Alicia Silverstone as Cher in Clueless.

Nicole Kidman wears a show stopping number in Moulin Rouge.

Diane Keaton as Annie Hall.

Sarah Jessica Parker as Carrie Bradshaw wearing Vivienne Westwood on her wedding day in Sex and The City: The Movie.

Catherine Bach as Daisy Duke in the classic Dukes of Hazard.

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Beyoncé sashayed into the rankings as one of the newest trendsetters in her "Single Ladies" music video.

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Madonna shocked the world as she took the stage for her 'Blond Ambition' tour in this Jean Paul Gaultier corset.

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Natalie Portman in Black Swan twirled and leaped into foreboding fantasy in her Rodarte designed costumes.

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Twiggy set a new precedent with her waif shape in the 1960s changing the body expectations for models forever and putting the London Invasion on the map.

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Julia Roberts completed her transformation from call-girl to catastrophically beautiful in a jaw dropping dress in Pretty Woman.

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Princesses Beatrice and Eugenie at the Royal Wedding, wearing nothing less than a party on their heads.

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Kate Hudson is show stopping in her gold gown in How to Lose A Guy In 10 Days.

Britney Spears performing live with a real boa...yikes!

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First Lady Michelle Obama at the Inauguration Ball.

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Olivia Newton-John playing Sandy in Grease, 1978.

Photo: Picture Credit: Christophel

Jackie O. breathed new life into the once stuffy White House becoming an accessible trendsetter for American women across the country.

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Uma Thurman in Pulp Fiction.

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Lil' Kim at the 1999 MTV Music Video Awards.

Photo: Picture Credit:WENN/ Sidewalk/Sidewalk Picture Group

The beloved Princess Diana at her wedding to Prince Charles.

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Elvis Presley sporting his iconic 70s white jumpsuit on his tour in Hawaii.

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Socialite Edie Sedgwick and legendary artist Andy Warhol broke down social barriers with their friendship and created a new sort of creative hub in Warhol's infamous Factory.

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Marlene Dietrich crossed gender boundaries in the 30s movie Morocco. This memorable pose in a mens' style suit is timeless and defines a new kind of style.

Photo: Picture Credit: Rex Features/

Kirsten Dunst took the silver screen by storm in her role as Marie Antoinette

Photo: Picture Credit: c.Sony Pictures/Everett / Rex Features/EVT

Elizabeth Hurley stole the show at the premiere of Four Weddings And A Funeral, when she wore this Versace safety pin dress!

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Glen Close plays evil but dashing Cruella de Vil in Disney classic 101 Dalmatians.

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How can anyone forget this jaw-dropping Guy Laroche gown worn at the Oscars by Hilary Swank?

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This picture speaks for itself. Pamela Anderson defined sexy bringing popularity back to the one-piece swimsuit in the hit TV series, Baywatch.

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Gwen Stefani is nothing short of a trendsetter. Here in 1998, she owns the blue hair while making her way down the red carpet.

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David Bowie in The Labyrinth.

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Yoko Ono and John Lennon took a stand for peace iconically in their statement style.

Ursula Andress' white belted bikini in the 1967 James Bond flick is nothing short of sassy beachwear.

Photo: Picture Credit: Rex Features/

Rita Hayworth defined screen siren in 1946 flick, Gilda.

Photo: Picture Credit: Rex Features/

For a couple of very violent bank robbers, Bonnie and Clyde had some serious style in the classic 1967 flick, Bonnie and Clyde.

Photo: Picture Credit: Warner Bros/

Kate Moss brought heroin chic to the masses with her tiny frame, becoming the face of mass retailers of brands like Calvin Klein in the 1990s.

Photo: Peter Lindbergh, Harper's Bazaar/

Molly Ringwald pretty much ruled the 80s. Winning our hearts in some of the most defining movies of the decade she looked adorably quirky in this gem, Pretty in Pink.

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In 1993, Naomi Campbell took a famous tumble down the Vivienne Westwood catwalk in impossible 10 inch platforms.

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With her androgynous looks and killer songs, Grace Jones set the stage for an entirely new kind of performer in the late 1970s into the 1980s.

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Pushing him into infamy, Michael Jackson's nearly fourteen minute "Thriller" video showed not only the singer's dance moves but also a peek into his imagination and creative force.


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