The Most-Talked-About Dresses of the Past 20 Years

Love them or hate them, the most-talked-about dresses of the past two decades may keep tongues wagging evermore. From Jennifer Lopez’s belly-button baring Versace ensemble at the 200o Grammy Awards to Kate Middleton’s breathtaking Alexander McQueen wedding gown complete with sweeping train, and Angelina Jolie’s black Atelier Versace number with an incredibly high slit from the 2012 Academy Awards—we've rounded up all the unforgettable looks here in celebration of InStyle’s 20th anniversary.

Is the dress you'll never forget in our roundup? Check out all the most talked-about dresses of the last 20 years now!

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1994: Elizabeth Hurley in Versace

Dave Benett

That dress is perhaps best known for demonstrating another handy use for safety pins: launching a career.

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1995: Uma Thurman in Prada

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Red carpets once belonged to only a handful of designers, and "stylist" just meant "hair-dresser." Après Uma, le déluge.

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1996: Carolyn Bessette in Narciso Rodriguez

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For chic brides, out went froufrou and in came minimalism and silk satin bias cuts.

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1997: Nicole Kidman in Dior

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Back in his glory days (before camera phones), John Galliano could start an orientalism trend with a single design: a shift based loosely on a cheongsam.

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1998: Madonna in Olivier Theyskens

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She favored young designers way before they were cool. Say what you will about this Frankendress, but she spotted Theyskens well before he became a star.

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1999: Gwyneth Paltrow in Ralph Lauren

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A gown could not have been sweeter had it been spun from cotton candy.

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2000: Jennifer Lopez in Versace

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The dress that crossed the belly-button divide also presaged an era of celebrities with increasingly naked ambitions. (Lopez even reprised the look on tour this year, minus the navel gazing.)

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2001: Renée Zellweger in Jean Dessès

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Calling someone old-fashioned suddenly became a compliment during the vintage craze brought on by this treasure from Lily et Cie.

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2002: Halle Berry in Elie Saab

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The best actress Oscar winner took home another award that night, for a daringly sheer dress likely to inspire fantasies for years.

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2003: Jennifer Lopez in Valentino

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Making history chic, her dress is based on a sari worn by Jackie Kennedy in 1967.

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2004: Charlize Theron in Gucci

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Sometimes everything goes just right, and the dress, hair, makeup, and accessories create an indelible image for the ages.

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2005: Hilary Swank in Guy Laroche

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Clean and sober in the front, scandalously plunging in the back, this dress could be described as the opposite of a mullet: It shows good taste.

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2006: Scarlett Johannson in Valentino

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More curve-hugging than a swimsuit on Baywatch, it's the sort of dress that causes men to lose their minds (even Isaac Mizrahi couldn't keep his hands to himself on the red carpet).

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2007: Reese Witherspoon in Nina Ricci

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Dressing well is the best revenge after a high-profile breakup, as shown in six shades of pleated silk jacquard.

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2008: Sarah Jessica Parker (as Carrie Bradshaw) in Vivienne Westwood

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Whose ultimate bridal fantasy does not include a headpiece shaped like a bird?

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2009: Michelle Obama in Jason Wu

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The fashionable First Lady anoints a star from the next generation of American designers.

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2010: Beyoncé in Armani Privé

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Shoulder pads make a comeback. And nothing says "outta-my-way" like a couture version large enough for a linebacker, when rendered in crystal-covered chain metal.

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2011: Kate Middleton in Sarah Burton for Alexander McQueen

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The world's most scrutinized royal wedding dress, kept secret until the last moment, combined the structure of Grace Kelly's gown with the media savvy of Princess Di's.

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2012: Angelina Jolie in Atelier Versace

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When your right leg spawns its own social-media following, you know you've created a moment. #jolieing

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2013: Miley Cyrus in Marc Jacobs

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It's strange to call a fishnet T-shirt dress classy, but, hey.

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2014: Rihanna in Adam Selman

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Showing up to collect a fashion-icon award in a nearly invisible crystal-mesh dress takes a lot of nerve. Of course, that's why she won.

Replay gallery

Forget Me Nots: The Most Talked-About Dresses of the Past 20 Years