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25 Unforgettable Dresses From the Past 25 Years

25 Unforgettable Dresses From the Past 25 Years

From the effortlessly elegant to the absolutely outrageous, here are the memorable outfits of the past quarter-century, according to stars, stylists, and EW's biggest fashion mavens.

By EW Staff

Updated October 13, 2015 at 01:00 PM EDT

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25 Unforgettable Dresses From the Past 25 Years

Credit: SGranitz/WireImage; Scott Gries/ImageDirect; Axelle/Bauer-Griffin/FilmMagic; Steve Granitz/WireImage; George Pimentel/WireImage

Click through to see stars' and editors' top picks from the past quarter-century.

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Diane Kruger in Giambattista Valli, 2012 Cannes

Credit: Mike Marsland/WireImage

"It's a flawless, timeless red-carpet moment that epitomizes elegance. Here she really is like a modern-day Grace Kelly. Pure class!" – Rosie Huntington-Whiteley, actress-model

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Michelle Williams in Vera Wang, 2006 Academy Awards

Credit: KMazur/WireImage

"Her saffron-colored gown would have been striking on its own, but paired with bold red lips and that chic side chignon, she graduated from TV teen to Hollywood royalty in an instant." – Meeta Agrawa, deputy editor, EW

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Helen Mirren in Christian Lacroix, 2007 Academy Awards

Credit: Frazer Harrison/Getty Images

"I get chills just remembering [this dress]. It skimmed her shape and accentuated her gorgeous curves. She wasn't trussed in and uncomfortable—she had this ease about her." – Tim Gunn, Project Runway

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Mariah Carey, 1991 Grammy Awards

Credit: AP Photo

"When you're as fabulous as 'Vision of Love'-era Mariah, you can rock a simple little black dress and still make heads turn." – Isabella Biedenharn, editorial assistant, EW

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Jennifer Lopez in Versace, 2000 Grammy Awards

Credit: Scott Gries/ImageDirect

"I just remember falling in love with her, because she seemed like she [stayed true to] her roots, which was really important. She just looked hot. Her t--s were made for the dress!" – Rita Ora, singer

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Jennifer Lawrence in Dior Couture, 2013 Academy Awards

Credit: Gregg DeGuire/WireImage

"It was simple and elegant but effortlessly demanded attention at the same time." – Lucy Hale, actress-singer

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Angelina Jolie in Atelier Versace, 2012 Academy Awards

Credit: Ethan Miller/Getty Images

"All I remember is her leg and the slit. I'll never forget that dress." – Constance Zimmer, actress

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Lizzy Gardiner in a dress she designed, 1995 Academy Awards

Credit: KMazur/WireImage

"I love dresses that show imagination, [and] that was an absolutely genius dress. I would wear it!" – Helen Mirren, actress

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Lady Gaga in Franc Fernandez, 2010 MTV VMAs

Credit: Jon Kopaloff/FilmMagic

"This is peak Gaga: kooky pretension that is either hilariously self-aware or hilariously self-unaware." – Darren Franich, senior writer, EW

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Julia Roberts in Vintage Valentino, 2001 Academy Awards

Credit: Mirek Towski/FilmMagic

"There was something so special about it, even though it was just black and white. It really had an impact on me." – Micaela Erlanger, stylist

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Nicole Kidman in Christian Dior by John Galliano, 1997 Academy Awards

Credit: Kevin Mazur/WireImage

"It was so chic — she looked like a princess." – Camilla Belle, actress

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Diana Ross in Gucci, 2003 Met Gala

Credit: Evan Agostini/Getty Images

"This classic shape brings out Diana's personality: sexy, glamorous, confident, and fun. And the fact that she actually twirled her way down the press line? Pure magic." – Nina Terrero, correspondent, EW

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Lizzy Caplan in Donna Karan Atelier, 2014 Emmy Awards

Credit: Jon Kopaloff/FilmMagic

"I loved this dress because it had an Old Hollywood feel but still felt very modern, sexy, and even a little edgy because of the cutouts." – Nina Dobrev, actress

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Kate Winslet in Ben de Lisi, 2002 Academy Awards

Credit: Steve Granitz/WireImage

"While a lot of times people go for broke at the Oscars, Winslet's simple red dress with a floral strap is the epitome of less is more." – Tim Stack, senior writer, EW

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Gwyneth Paltrow in Ralph Lauren, 1999 Academy Awards

Credit: Evan Agostini/Getty Images

"There was something timeless and classic that she really pulled off. And I love that she chose pink, not the usual black or metallic. It's elegant and super feminine." – Lisa Berman, photography director, EW

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Erykah Badu in Givenchy, 2014 Met Gala

Credit: George Pimentel/WireImage

"It looked amazing, because she wasn't dressed like everyone else. It was really clean... but there was a lot going on at the same time." – Zendaya, actress

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Kate Hudson in Atelier Versace, 2014 Academy Awards

Credit: Axelle/Bauer-Griffin/FilmMagic

"That cape did it for me — she looked sexy, stylish, and classic but still modern." – Ashley Madekwe, actress

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Cate Blanchett in Valentino Couture, 2005 Academy Awards

Credit: SGranitz/WireImage

"Cate [looks] timeless, confident, elegant, and strong." – Kate Bosworth, actress

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Björk in Marjan Pejoski, 2001 Academy Awards

Credit: Mirek Towski/FilmMagic

"I just love that she didn't give a s---. This was just so whimsical." – Angela Lindvall, actress-model

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Julianne Moore in Givenchy Haute Couture, 2015 SAG Awards

Credit: Jon Kopaloff/FilmMagic

"There's nothing I love more on a redhead than emerald green. I never get tired of that. She looks so breathtaking, and perfectly sexy but elegant and classy." – Rachel Zoe, stylist

Continued on next slide.

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Madonna in Givenchy, 1996 Evita Premiere

Credit: SGranitz/WireImage

"I still have a photo of this from my wall. It makes my heart sing." – Salvador Perez, Jr., costume designer for The Mindy Project and Pitch Perfect

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Sharon Stone in a Gap shirt and Vera Wang with Phil Bronstein, 1998 Academy Awards

Credit: Evan Agostini/Getty Images

"Sharon Stone wears the Gap? I wear the Gap! She proved that attitude — not money or labels — wins the red carpet every time." – Henry Goldblatt, editor, EW

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Elizabeth Hurley in Versace with Hugh Grant, 1994 Four Weddings and a Funeral Premiere

Credit: Dave Benett/Getty Images

"J. Lo's green Versace dress never would have existed if not for this jaw-dropping black gown." – Lynette Rice, editor at large, EW

Continued on next slide.

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Britney Spears with Justin Timberlake, 2001 American Music Awards

Credit: Jeffrey Mayer/WireImage

"Britney and Justin in denim: the first thing that comes to mind [about red carpet looks] are the most ridiculous things." – Jerrika Hinton, actress

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Juliette Lewis in vintage with Brad Pitt, 1992 Academy Awards

Credit: Jim Smeal/WireImage

"The dress itself was very simple, but she threw everyone a curveball with the cornrows... and she had Brad Pitt on her arm, which doesn't hurt." – Chloë Sevigny, actress

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Up Next

By EW Staff

Account

25 Unforgettable Dresses From the Past 25 Years

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25 Unforgettable Dresses From the Past 25 Years

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Diane Kruger in Giambattista Valli, 2012 Cannes

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Michelle Williams in Vera Wang, 2006 Academy Awards

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Helen Mirren in Christian Lacroix, 2007 Academy Awards

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Mariah Carey, 1991 Grammy Awards

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Jennifer Lopez in Versace, 2000 Grammy Awards

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Jennifer Lawrence in Dior Couture, 2013 Academy Awards

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Angelina Jolie in Atelier Versace, 2012 Academy Awards

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Lizzy Gardiner in a dress she designed, 1995 Academy Awards

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Lady Gaga in Franc Fernandez, 2010 MTV VMAs

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Julia Roberts in Vintage Valentino, 2001 Academy Awards

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Nicole Kidman in Christian Dior by John Galliano, 1997 Academy Awards

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Diana Ross in Gucci, 2003 Met Gala

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Lizzy Caplan in Donna Karan Atelier, 2014 Emmy Awards

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Kate Winslet in Ben de Lisi, 2002 Academy Awards

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Gwyneth Paltrow in Ralph Lauren, 1999 Academy Awards

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Erykah Badu in Givenchy, 2014 Met Gala

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Kate Hudson in Atelier Versace, 2014 Academy Awards

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Cate Blanchett in Valentino Couture, 2005 Academy Awards

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Björk in Marjan Pejoski, 2001 Academy Awards

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Julianne Moore in Givenchy Haute Couture, 2015 SAG Awards

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Madonna in Givenchy, 1996 Evita Premiere

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Sharon Stone in a Gap shirt and Vera Wang with Phil Bronstein, 1998 Academy Awards

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Elizabeth Hurley in Versace with Hugh Grant, 1994 Four Weddings and a Funeral Premiere

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Britney Spears with Justin Timberlake, 2001 American Music Awards

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Juliette Lewis in vintage with Brad Pitt, 1992 Academy Awards

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