Best Worst Dressed

The Best and Worst Dressed People of All Time

UPDATED 09/18/2000 at 01:00 AM EDT Originally published 09/18/2000 at 01:00 AM EDT

How did Princess Diana shift from shy to sexy–and get the world to follow suit? The same way Jackie Kennedy got her sisters-in-style to follow suits (and pillbox hats). With taste, luck–and attitude. As for the eyesores on our list, well, there's a place for them too. Says designer Randolph Duke of a certain country music queen: "Women shouldn't dress in a Dolly Parton collection, but for her...her style makes me smile."

PRINCESS DIANA
Just 20 when she married Prince Charles in 1981, Diana (1961-1997) separated herself from stodgy royal style–and became an international icon. She started off in polka dots and ruffles, but with help from a legion of designers she soon began going hat-less, gloveless and even strapless. After splitting with Charles in 1992, she cut even looser, flaunting her gym-toned figure in minidresses and slinky gowns (left, in Catherine Walker In 1996). As Elizabeth Emanuel, who designed her wedding dress, says, "She injected that fashion element into the royal family. Because she was so good-looking and model-like, she got away with it."

COCO CHANEL
"I am first and, finally, my only model," designer Coco Chanel (1883-1971) declared. Her tailored, precise suits, jersey twinsets, long strands of pearls and of course the little black dress endure today. Chanel (above, in the late '40s) "was so forward-looking for that era," says fashion designer Amsale. "To this day the look is incredibly beautiful."

AUDREY HEPBURN
Nobody ever looked like her before World War II...and the proof is that thousands of imitations have appeared," photographer Cecil Beaton wrote in Vogue in 1954. Decades later, women are still inspired by Audrey Hepburn (1929-1993), who set trends for ballet flats, sleeveless dresses, bateau-neck tops, capri pants and pixie haircuts (left, ca. 1956). "There was a simplicity about how she created a look," says socialite Blaine Trump. "She established that 'less is more.'"

LENA HORNA
Her formula for success was to mix the understated (say, a hairdo) with the flashy (a riveting gown). "Her look was elegant but bold," says designer Jeffrey Banks. The singer and actress, now 83, also broke a color barrier in fashion. Her dramatic outfits in striking hues (left, ca. 1953) made her "a very good role model," says fashion historian Kathleen Craughwell-Varda. "She showed us that we can wear many colors."

CARY GRANT
The star's archetypal status comes from a combination of perfect tailoring and perfect nonchalance. Cary Grant (1904-1986) knew what it took to make him look his best. "He had a wide head," says designer Alan Flusser, "so he wore his shoulders wider to balance it." Yet however impeccable the suit (right, ca. 1938), he always appeared playful and relaxed. Grant's style, says Flusser, "was very simple, but reeking of suaveness."

BABE PALEY
When Babe Paley died in 1978 at 63, she was eulogized as "a beacon of perfection" who guided women toward impeccable taste. The former Vogue editor and wife of CBS founder Bill Paley helped popularize shift dresses, which featured the unfussy lines she favored (even in ball gowns, above, in 1954). W editor-at-large John Fairchild recalls, "She never had a hair out of place, and her suits were always well-cut with a jewel perfectly in place."

TOM CRUISE
Since he sparked sales of Ray-Ban Wayfarers after 1983's Risky Business, Cruise, 38 (above, in January), has had it made in the shades. It's sartorial sleight of hand that gives him an edge, says designer Jeffrey Banks: "He's bigger than life onscreen, but he's really not that tall [5'9]. He understands how to use clothes to his best advantage."

JACKIE KENNEDY ONASSIS
The Queen of Camelot was a gust of cosmopolitan style blown into a White House unfamiliar with dazzling evening wear, sleek suits and saucy pillbox hats (below, in 1961). Later, as the wife of Aristotle Onassis, she adopted the oversize sunglasses, trench coats and simple trousers that remained her signature until she died in 1994 at age 64. "Her impact on fashion was universal and constant," says Oleg Cassini, who designed her White House wardrobe. "She wore clothes that looked and are eternal."

PETER JENNINGS
ABC's top anchorman doesn't just have a nose for news–he also has an unerring fashion sense. "I look at the tie, the cut of the collar, the color of the shirt, the texture of the jacket," says CNN style expert Elsa Klensch of Peter Jennings, 62 (above, in 1999). "There's a great eye that puts it all together."

THE DUCHESS AND DUKE OF WINDSOR
When Edward VIII (1894-1972) abdicated the British throne in 1936 to marry American divorcée Wallis Simpson (1896-1986), he starred in one of the world's greatest love stories–and became part of the century's most influential fashion couple (above, in 1940). The duke popularized baggy pants on the golf course, endorsed the mixing of plaids with checks and stripes, and taught men how to tie their neckties in what is now known as the Windsor knot. The duchess amassed a much-copied jewelry collection that sold at auction in 1987 for $50 million, inspired women to wear high-necked evening gowns, and established the dictum that skirts must fall precisely to the knee. "They had nothing else really to do except worry about how they looked," says fashion author Kathleen Craughwell-Varda. "So their clothes were pretty fantastic up until the end."

RICHARD GERE
Suited in sleek Armani for the 1980 film American Gigolo (above), Richard Gere taught men to cast aside their boxy wool suits and drape themselves in tailored jackets and pants made of fine, relaxed fabrics. Now 51, the actor still has "international impact," says fashion industry analyst Tom Julian. "And he does a tux better than anyone."

FRED ASTAIRE
He danced with astonishing grace in a top hat and tails, but Fred Astaire (1899-1987) was actually a pioneer of casual dress. He helped usher in khakis, button-down shirts and natural-shouldered jackets. He also fueled a fad for using a necktie as a belt (above, in 1934). "He was trailblazing in terms of fashion," says menswear designer Alan Flusser, who adds, "He wore interesting shoes and colorful socks. He did more for hosiery than any other performer."

GRACE KELLY
She embodied High Society with her white gloves, nipped-in jackets and crisp ball gowns (right, at the 1956 Academy Awards). And as Princess Grace of Monaco following her April 1956 wedding to Prince Rainier, this well-bred Philadelphia girl (1929-1982) was so adored that when she held a large Hermes bag over her belly to discreetly conceal her first pregnancy, the purse became an enduring status item, known as the Kelly bag. Recalls her onetime fiancé, designer Oleg Cassini: "She dressed like a lady."

KATHARINE HEPBURN
When she began her movie career in the 1930s, women were discouraged from wearing pants on the studio lots. Hepburn, now 93, flouted convention, dressing in what she called "my uniform"–trousers often topped with a man-tailored jacket and shirt. "She was going after freedom and comfort," says fashion historian Sandy Schreier. "And she was saying, 'I'll do what I want.'"

JOHN F. KENNEDY
By refusing to wear the traditional baggy suit or sober hat, John F. Kennedy (1917-1963) put a new spin on what it meant to look like a leader (as he does above, in the Oval Office in 1962)–and led men across the country to do the same. "Everything about him was perfectly put together," says Frankie Hewitt, an artistic director at the Ford Theatre in Washington, D.C. "When you see film of him, nothing seems dated. If he had walked into the convention this year, he would have looked just right."

WARREN BEATTY
The 63-year-old star (above, in '91) of such trend-setting movies as Bonnie and Clyde and Shampoo has stayed au courant throughout his career. "His fashion has been as important as the twinkle in his eye," says makeup artist Michele Probst.

BILL COSBY
In the '80s, he was America's favorite TV dad. And with his colorful sweaters, Bill Cosby, 63 (below, in 1991), made parenthood look hip. Says fashion industry analyst Tom Julian: "He was a cool dad who dressed cool, on TV and in real life."

BARBARA WALTERS
Whether interviewing Richard Nixon in China or drawing tears from Monica Lewinsky, Walters, 68 (below, in 1996), has been precisely where a newswoman should be: in the moment. "If she's on somebody's ranch, she's dressed in pants and a sweater–not high heels," says designer Arnold Scaasi. "She set the standard for how women journalists on TV dress today."

TAMMY FAYE BAKKER MESSNER
During her '80s heyday she was as famous for her cartoon-like style as for the popular TV ministry she shared with then-husband Jim Bakker. With tattooed-on makeup, gargantuan jewelry and outré outfits (like the yellow suit below, in '96), she became a fashion joke. Now 58 and wed to developer Roe Messner, she recently said, "I'm probably a bit more dramatic than most people would like me to be, but...that's just who I am."

ELIZABETH TAYLOR
"'The more the better' has always been my motto," Taylor, 68, once said. The acquisitive actress (above, in 1971) has collected millions of dollars' worth of jewelry from seven husbands, but when it comes to displaying it, her more-is-more philosophy falls apart. "There's just too much decoration," says fashion forecaster David Wolfe. "The big jewelry on top of the overstated outfits with the larger-than-life hairdos–she never knows when to stop."

DOLLY PARTON
As she herself famously declared, "It takes a lot of money to look this cheap." The country star's unnatural assets include some 300 wigs, a few surgical enhancements–and a wardrobe (such as this '88 gown, below) that shows it all off. Parton, 54, "goes over the top," says designer Nolan Miller. "It makes her a caricature."

MARIAH CAREY
Favoring hiked-up hemlines and plunging necklines, the 31-year-old singer (above, in a crocheted minidress at the 1999 Billboared Music Awards) "wants to be glamorous," says designer Amsale, "but she ends up looking silly."

ROSEANNE
She went from struggling waitress to millionaire sitcom star on the strength of her outsize personality–a trait that Roseanne, 47 (above, in red leather at the '92 Emmys), extends to her wardrobe. "She's someone who dresses to get the worst possible headline," says fashion industry analyst Tom Julian.

QUEEN ELIZABETH II
The British monarchy has always been resistant to change. So it's not surprising that Queen Elizabeth II, 74, has followed the same fashion rules–a dress or suit with matching shoes, bag and hat (below)–throughout her 47-year reign. "The formula is so outdated–she is kind of stuck in a look," says fashion historian Kathleen Craughwell-Varda.

DENNIS RODMAN
The title of his autobiography is Bad As I Wanna Be, and during 13 NBA seasons Dennis Rodman lived up to that motto. The 6'8" hoopster turned to body piercings and neon hair dye to stand out among his teammates. Out of uniform, Rodman, 39, wrapped himself in feather boas and silver belly chains (above, at a 1996 talk show taping). "Sometimes bad taste just stares you in the face," says designer Victor Costa.

PAMELA ANDERSON LEE
With her big blonde hair and even bigger cleavage always on display (in this case at the '99 MTV Video Music Awards), Pamela Anderson Lee, 33, presents herself as a Hollywood bombshell. But, says fashion historian Sandy Schreier, "she overdoes it."

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