Brooke Shields, 1980

Mr. Blackwell's Worst

Does this "Pretty Baby" look worse than anyone else did in 1980? The worst part of Brooke Shields' outfit is her clownish makeup job. (Photo by Ronald Reagan Library/Getty Images)

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Brooke Shields, ... Does this "Pretty Baby" look worse than anyone else did in 1980? The worst part of Brooke Shields' outfit is her clownish makeup job. (Photo by Ronald Reagan Library/Getty Images)
Barbara Mandrell... Country chanteuse Barbara Mandrell (left) was a big star in music and TV in the '70s and '80s, but her outfits were not a hit with Mr. Blackwell. Photo by Kevin Winter/Getty Images.
Princess Diana, ... She would eventually become a major style icon, but it took Lady Di a while to grow into that role. In the early years, she tended towards dowdy, prim frocks that seemed more schoolgirl than future Queen of England. (Photo by Jayne Fincher/Getty Images)
Joan Collins, 19... The ageless "Dynasty" star has worn everything from fur mukluks to shoulder pads so large they should have their own zip code, but the biggest faux pas of Ms. Worst-Dressed of 1983 is her teetering tousle of asymmetrical hair. (Photo by Keystone/Getty Images)
Cher, 1984 Blackwell put Cher in his crosshairs even before she wore this infamous Bob Mackie creation to the 1986 Oscars. It would not be the last time that the singer-actress would appear on his list. (AP Photo/Lennox McLendon)
Princess Stephan... Another royal disappointment in Mr. Blackwell's eyes. The 'wild child' Princess Stephanie dated a circus owner and occasionally dresses like she's in one herself. (Photo by Pascal Le Segretain/Getty Images)
Meryl Streep, 19... Streep is tops in acting talent, but her style sense seems to run more in the direction of museum docent than major Hollywood star. (Photo by Brenda Chase)
Lisa Bonet, 1987 "The Cosby Show" and "A Different World" star has always cut her own path, but outfits like this give 'bohemian chic' a bad name - and perhaps gave Mary-Kate Olsen an idea of what was stylish. (Photo by Brenda Chase)
Sarah Ferguson, ... Fergie, the Duchess of York (not to be confused with Fergie, the Dutchess of Lady Lumps) took a lot of lumps for her weight and free-spirited nature, but for Mr. Blackwell, her worst sin was donning outfits like this tartan terror. (AP Photo/Charles Miller)
La Toya Jackson,... Mr. Blackwell usually chose big stars as his worst-dressed, but he appears to have made an exception in 1988 by including the pseudo-celeb La Toya Jackson. Perhaps wearing an outfit made of shredded toilet paper made him overlook his usual requirements? (Photo by Frederick M. Brown/Getty Images)
Sinead O'Connor,... Nothing compares to Sinead O'Connor's kooky outfits. Really, what does one wear to rip up the Pope's picture? (Photo by Getty Images)
Julia Roberts, 1... We couldn't find any egregious examples of the "Pretty Woman" looking terrible, except when she was in costume as the hooker with a heart of gold in the movie that launched her into superstardom. (Photo By Getty Images)
Madonna, 1992 Mr. Blackwell called her Madgesty "the bare-bottomed bore of Babylon" and didn't care for any of her looks, from her Boy Toy-belt-buckle-wielding days to the conical-bustier-and-garters she favored in th '90s. (AP Photo/FILE)
Glenn Close, 199... It seems that everyone's favorite 'other woman' has a "Fatal Attraction" to frumpy clothing. (Photo: Keith Bedford/ImageDirect)
Camilla Parker B... The other woman in Prince Charles's life, Camilla Parker Bowles, also made it on to Mr. Blackwell's list, where he named her "the Duchess of Dowdy." Maybe palling around with the prince does damage to these ladies' fashion sense? (AP Photo/Robin Nowacki)
Howard Stern, 19... It took him long enough, but finally Mr. Blackwell started including the fashion-challenged fellas in Hollywood on his worst-dressed list. First up, the schlumptastic shock jock Howard Stern... (Photo by Evan Agostini/Getty Images)
Dennis Rodman, ... ...followed by cross-dressing basketball star and fashionista Dennis Rodman. (Photo By Getty Images)
Spice Girls, 199... He couldn't pick just one, so Mr. Blackwell named all five Spice Girls as his worst-dressed. It's hard to believe, but that person in the middle there is Posh and there appears to be actual flesh on her bones! From left to right: Melanie Chisolm (Sporty), Geri Halliwell (Sexy), Victoria Addams (Posh), Melanie Brown (Scary) and Emma Lee Bunton (Baby).
Linda Tripp, 199... What is Pentagon employee Linda Tripp doing on this list? She's not a celeb, singer or a royal. She may have been in the public eye in 1998 for her role in the Lewinsky-Clinton affair, but we still think this is a cheap shot on Mr. Blackwell's part. (AP Photo/Doug Mills)
Cher, 1999 Cher made it back on the list in 1999 and based on this golden getup, a second appearance was justly deserved. Blackwell called her "the ultimate fashion fiasco." (Photo by Frederick M. Brown/Getty Images)
Britney Spears, ... It's just not fair that Spears was the only one singled out by Mr. Blackwell. We think Justin "Jean Suit" Timberlake looks far worse in his denim disaster than Brit-Brit. (AP Photo/Mark J. Terrill)
Anne Robinson, 2... "Weakest Link" host Anne Robinson is definitely the weakest link on Mr. Blackwell's list. (Photo: Chris Hasto / NBC / Getty Images)
Anna Nicole Smit... Despite a re-energized career for the former Guess model in the early 2000s, including a TrimSpa spokesmodel gig and a reality show (and eventually a sad descent into drug abuse), Mr. Blackwell was not impressed with Smith's Southern-fried sartorial sense. (Photo by Kevin Winter/Getty Images)
Paris Hilton, 20... It was just Paris who earned Blackwell's ire for her skanky socialite looks, but sister Nicky (right) seems just as deserving. (AP Photo/Damian Dovarganes)
Nicollette Sheri... Mr. Blackwell was "Desperate" to smack down Nicollette Sheridan in 2004. (Photo by Stephen Shugerman/Getty Images for AFI)
Britney Spears, ... It only took Mr. Blackwell five years to deliver another slap in the face to Britney's sense of style. (AP Photo/Joe Cavaretta)
Paris & Britney,... Mr. Blackwell was so offended by these two that he split the worst-dressed honors in 2006, after naming each of them individually in previous years. He called them "two peas in an over-exposed pod." (Paris Photo by Andrew H. Walker/Getty Images; Britney Photo by Matthew Simmons/Getty Images for Rolling Stone)
Victoria 'Posh' ... Posh's second appearance on Mr. Blackwell's list is a solo act. (Photo by Jens Koch/Getty Images)
Mr. Blackwell (A... Mr. Blackwell was born Richard Selzer and worked as an actor and fashion designer before establishing a career as a couture critic. His worst-dressed list has appeared annually since 1960. (Photo by Chad Buchanan/Getty Images)