1Joan Bennett, January 1928
Getty ImagesJoan Bennett kept with traditional flapper style—a drop waist and a paneled hem—but the black color makes it timeless.
2Lauren Bacall, December 1944
Getty ImagesLauren Bacall dresses up her v-neck LBD with a four-strand pearl choker—and, of course, her killer stare.
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3Elizabeth Taylor, January 1950
Getty ImagesThe full skirt and tight bustier of Elizabeth Taylor's dress was the epitome of style in the 1950s, but rather than follow the bright print and pattern trend of the time, the young starlet opted for a simple black fabric.
4Sophia Loren, 1955
Hulton Archive//Getty ImagesActress Sophia Loren proves that there's no limit to what you can do with a LBD with this pleated and nautical design she wore in Cannes.
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5Marilyn Monroe, July 1956
Getty ImagesMarilyn Monroe's chic figure-hugging black sheath dress proves that less is always more.
6Audrey Hepburn, June 1961
Getty ImagesGivenchy was chosen to design Audrey Hepburn's iconic black sheath dress that she wore in the opening scene of Breakfast at Tiffany's.
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7Joan Crawford, October 1962
Getty ImagesJoan Crawford opted for a tulle scoop neck black dress when she appeared on The Tonight Show starring Johnny Carson.
8Sophia Loren, 1965
Getty ImagesSophia Loren knew how to travel in style, which is why the actress opted for a belted black coat dress and cheetah print hat while flying with TWA in the '60s.
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9Catherine Deneuve, September 1966
Getty ImagesFrench actress Catherine Deneuve added a bit of flair to her simple black dress with a gold square belt and metal embellishments.
10Jaqueline Kennedy, September 1970
Getty ImagesIn true '70s style, Jackie Kennedy stepped out of her New York City apartment wearing a chic chiffon and ruffled sleeved black dress.
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11Madonna, November 1985
Getty ImagesThe "Like a Virgin" singer was known for her theatrics, which is why she shocked fans with her simple yet sophisticated black dress on Saturday Night Live.
12Kate Moss, January 1990
Getty ImagesA young model at the time, Kate Moss's black dress with a high neck and cut out details wowed on the red carpet alongside her boyfriend, Johnny Depp.
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13Princess Diana, June 1994
Getty ImagesPrincess Diana's off the shoulder, form fitting silk little black dress has been labeled "the revenge dress" as she wore it the same night Prince Charles aired his tell-all documentary about the couple's marriage and subsequent divorce. Although Diana didn't make a statement that night, her LBD spoke volumes.
14Sarah Jessica Parker, January 1995
Getty ImagesPre-Carrie Bradshaw, Sarah Jessica Parker flexed her style skills in a short black slip dress and sheer tights.
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15Reese Witherspoon, September 1997
Getty ImagesIf we could personify the '90s into one dress, Reese Witherspoon's spaghetti strap black mini dress for the House of Yes premiere would be it.
16Gwyneth Paltrow, November 2000
Getty ImagesGwyneth Paltrow took the little black dress to a whole new level at the Bounce premiere in 2000. The starlet opted for a strapless, knee-length, and ruched version of the classic.
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17Mischa Barton, December 2003
Getty ImagesThe open slit and one shoulder cut on Mischa Barton's Billboard Music Awards dress gives the look a modern spin.
18Naomi Campbell, February 2006
Getty ImagesThe below the knee length on Naomi Campbell's silk corset dress keeps the look sophisticated and classic.
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19Angelina Jolie, May 2007
Getty ImagesAngelina Jolie looked demure in a black lace dress at the Cannes Film Festival with Brad Pitt.
20Charlize Theron, June 2008
Getty ImagesAt the Hancock premiere in London Charlize Theron rocks the red carpet in a peplum black dress with a sky-high slit.
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