The Ten Most Iconic Fashions Ever

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  • Some of them are fabulous; others are fabulously bad. But these ten outfits have survived over the decades as the most memorable fashions ever.

    Marilyn Monroe: The John F. Kennedy Dress

    Monroe wore this glittering Jean Louis style when she famously sang “Happy Birthday” to JFK at his Madison Square Garden birthday part in 1962. Reportedly, it was so tight that she wore nothing underneath. It sold at auction for $1.26 million.
  • Audrey Hepburn: The Little Black Dress Hepburn wore it short and long, in Breakfast at Tiffany’s and offscreen. The Givenchy design, set off by Hepburn’s gamine beauty, started the LBD (little black dress) craze that continues to this day. It sold at auction for $807,000.
  • Jacqueline Kennedy: The Pink Suit During her time in the White House, the First Lady was a fashion icon, wearing long white gloves, pink satin evening gowns and pillbox hats. But it’s a tragic reality that the style she’s most remembered for is the pink suit she wore on Nov. 22, 1963, the day her husband was assassinated in Dallas.
  • Twiggy: The Mini Dress The super-skinny model with the enormous eyes would have made an impact no matter what she wore. But she popularized the revolutionary mini-dress, which hit six or seven inches above the knee and was designed by the swinging London fashionista Mary Quant.
  • Diane von Furstenberg: The Wrap Dress In the 1970s, the little wrap dress was embraced by literally millions of women who took it from the office to the evening (probably at a singles bar.) It was perfect: It came in a lot of different prints and the cinch style defined your waist as well as forgiving the pound or two you might have gained recently. In a 21st-century incarnation, it’s still being sold today.
  • Linda Evans: The Fullback Dress In the 1980s, when Dynasty ruled, the point of the dress was shoulders. Big shoulders, with pads that could have doubled as knee supporters for athletes. The shoulders were supposed to define your silhouette and make you look like a Boss Lady, but let’s face it, most of the time the broad shoulders gave us the look of a wide receiver on the Dallas Cowboys.
  • Cher: The Drag-Queen Dress Before Cher came on stage at the 1986 Academy Awards, Jane Fonda told the audience, “Wait’ll you see what’s going to come out here.” The giant Mohawk headdress was a perfect complement to the gauzy, glittery material that covered the most risqué body parts—and nothing more. Is it any surprise that it was designed by the “rajah of rhinestones,” Bob Mackie?
  • Diana, Princess Of Wales: The Revenge Dress By 1994, thirteen years after she married Prince Charles in a dress that looked like 50 pounds of marshmallows, Diana had become a fashion idol. Perhaps her best dress was the one she wore the night that Charles publicly acknowledged his affair with Camilla Parker Bowles. Short, fitted and finished off with a killer choker, it said, “I’ll always get a lot more attention than you, you silly little man.”
  • Bjork: The Swan Dress There are some dresses we can’t forget; others haunt us (and not in a good way). The swan dress worn by the Icelandic singer Bjork to the 2001 Oscars fits into the latter category. Created by the Macedonian designer Marjan Pejoski, it consisted of a body stocking covered with a feathered reproduction of a swan. It managed to be both tasteless and laughable, but Bjork went on to wear it many times. Unfortunately.
  • Kate And Pippa Middleton: Bride And Bridesmaid When Kate Middleton married Prince William earlier this year, all eyes were on her – until her sister Pippa stepped out of the wedding limo. As Pippa arranged Kate’s train, it was hard, at least for male viewers, to tear their eyes away from the bridesmaid’s perfectly fitted cream-colored dress. (Both were designed by Sarah Burton for Alexander McQueen.) This is probably one of the few times in wedding history that a bridesmaid has actually been happy with her dress.