April 03, 2004 01:00 AM

PRINCESS DIANA: BEST OF THE BEST
The late Princess of Wales reigned over PEOPLE’s best dressed list, hitting the jackpot a record nine times.

Princess Diana had admirers the world over, but her sense of style made her a true icon among the fashion-conscious, and she remains PEOPLE’s best-dressed woman of all time – though with a brief visit to the worst-dressed list in 1991.

The epitome of grace and classic beauty, Diana brought a fresh look into the House of Windsor and inspired global fashion trends still present on today’s style scene. The princess, who was killed in a car crash six years ago, possessed a natural, enviable ability to wear everything well, and whether dressed to the nines or lounging in jeans and sweaters, she could be counted on to dazzle and delight.

MADONNA: WORST OF THE WORST
The ever-morphing Material Girl, having hit the worst-dressed list seven times, is in desperate need of some new material.

With her relentless pursuit of success, her in-your-face attitude and her peerless ability to transform her image, this pop icon has managed to achieve and maintain global super-stardom for more than two decades. Who’s that girl? Madonna, of course! Yet her ever-changing look, though always daring and eye-catching, has led the 45-year-old from bad to worse so many times that she steals the show as PEOPLE’s worst-dressed celeb. The only other star who has earned the dubious distinction of seven spots on the worst-dressed list is Cher.

DEMI MOORE: FLIP-FLOP
Since getting on PEOPLE’s fashion radar in 1985, Moore has been recognized six times, serving equal time on the best- and worst-dressed lists.

Demi Moore’s unique name may say more about her than we thought. While “demi” – the French word for “half” – fails to describe her schedule, which is filled with acting, producing and motherhood, it certainly does justice to her sense of style. The unpredictable actress, 40, seems to step up to the fashion plate blindfolded, with an equal number of grand slams and strikeouts throughout the years. From 1989’s awful unitard to 2001’s gold-medal gown, Moore may be stuck in the middle of the style spectrum, but she never fails to get our attention. MICHAEL JACKSON: BEST TO WORST
Jackson went from best dressed in 1984 to two turns on the wrong side of the fashion tracks.

He may be known as the King of Pop, but when it comes to style, Michael Jackson, 45, is more like the court jester – after all, his fashion choices are often as wacky and unexpected as his behavior. Luckily for him, the ’80s encouraged wardrobe experimentation, and few dared voice the question “Where’s the other glove?” But since then, the rules of the fashion game have changed, and these days, Jackson is in the penalty box.

SARAH JESSICA PARKER: WORST TO BEST
She’s a fashion plate now – proven by her twin honors as PEOPLE’s best dressed – but this shining star once made red-carpet watchers balk.

Sarah Jessica Parker’s character on Sex and the City may seem to have innate fashion sense, but in real life Parker landed on PEOPLE’s best-dressed list only after much trial and error. These days she sports all the hottest new looks, but back in 1987, Parker, now 38, was a fashion victim. It’s comforting to know that even the most enviably fashionable stars have a few skeletons in their closets. Best Dressed
Sneak a peek at the chic celebs who have topped PEOPLE’s annual list the most.

NINE
Princess Diana (1981, 1982, 1983, 1984, 1986, 1987, 1988, 1989, 1992)

SEVEN
Prince William (1983, 1986, 1988, 1989, 1996, 2000, 2001)

FIVE
Gwyneth Paltrow (1996, 1998, 1999, 2001, 2002)
Julia Roberts (1990, 1991, 1999, 2001, 2002)

FOUR
Oprah Winfrey (1991, 1994, 1995, 2001)
Diane Sawyer (1982, 1999, 2001, 2002)
George Clooney (1995, 1997, 2000, 2001)

THREE
Jennifer Aniston (2000, 2001, 2002)
Sandra Bullock (1996, 1998, 2002)
Brandy (1996, 1998, 2001)
Demi Moore (1987, 1990, 2001)
Heather Locklear (1994, 2000, 2001)
Nicole Kidman (1995, 2001, 2002)
Charlize Theron (2000, 2001, 2002)
Catherine Zeta-Jones (1999, 2001, 2002)
Minnie Driver (1998, 2001, 2002)
Will Smith (1999, 2001, 2002)
Prince Harry (1989, 2001, 2002)
Sarah Jessica Parker (1994, 2001, 2002)

TWO
Jada Pinkett Smith (2001, 2002)
Hugh Grant (1994, 2002)
Puff Daddy (1998, 2002)
Sarah Michelle Gellar (2001, 2002)
Jessica Alba (2001, 2002)
Selma Blair (2001, 2002)
Mandy Moore (2001, 2002)
Lisa Ling (2001, 2002)
Debra Messing (2001, 2002)
Kate Beckinsale (2001, 2002)
Kate Hudson (2001, 2002)
Halle Berry (2001, 2002)
Angela Bassett (2001, 2002)
Reese Witherspoon (2001, 2002)
Elizabeth Hurley (1995, 2002)
Uma Thurman (2001, 2002)
Tom Cruise (2000, 2002)
Harrison Ford (1997, 2002)
Mel Gibson (1989, 2002)
Michael Michelle (2001, 2002)
Denzel Washington (1990, 1995)
Peter Jennings (1982, 1992)
Brad Pitt (1999, 2001)
Cindy Crawford (1991, 1995)
John Travolta (1980, 1982)
Brooke Shields (1980, 1982)
Prince Charles (1981, 1982)
John F. Kennedy Jr. (1981, 1985)
Sharon Stone (1992, 1993)
Christie Brinkley (1982, 1984)
Jack Nicholson (1984, 1986)
Sylvester Stallone (1982, 1991)
Elizabeth Taylor (1986, 1987)
Benjamin Bratt (2001, 2002)
Penelope Cruz (2001, 2002) Worst Dressed
For shame! Meet the star offenders who have landed on PEOPLE’s worst-dressed list most often.

SEVEN
Madonna (1985, 1987, 1988, 1989, 1990, 1992, 1999) Cher (1980, 1986, 1988, 1989, 1996, 1999, 2001)

SIX
Daryl Hannah (1988, 1990, 1991, 1992, 1993, 2001) Sarah Ferguson (1987, 1988, 1989, 1990, 1992, 1994)

FOUR
Goldie Hawn (1984, 1989, 1991, 2001)

THREE
Raquel Welch (1985, 1988, 2001)
Jean Casem (1986, 1988, 1992)
Roseanne (1989, 1990, 1992)
Cyndi Lauper (1986, 1987, 1988)
Demi Moore (1989, 1992, 1995)
Ivana Trump (1990, 1992, 2001)
Cybill Shepherd (1986, 1987, 2001)
Christina Aguilera (2000, 2001, 2002)
David Arquette (1999, 2001, 2002)
Jennifer Love Hewitt (2000, 2001, 2002)
Pamela Anderson (1995, 2001, 2002)

TWO
Michael Jackson (1992, 2001)
Drew Barrymore (1984, 1995)
Geena Davis (1989, 1992)
Bruce Willis (2000, 2001)
Alex Kingston (1998, 2002)
Bianca Jagger (1988, 2002)
Helena Bonham Carter (2001,2002)
Hillary Clinton (1994, 2002)
Julia Roberts (1991, 1993)

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