Fashionable or faux pas? Click on the arrow at right to weigh in on Brooke Shields and other celebs who pushed the envelope.
Charles Eshelman/FilmMagic - AP Photo/Peter Kramer
Brook Shields stepped out at the NYC Ballet's 2011 spring gala on wearing a one-shouldered black dress and a frilly, feathered flower necklace.
Jessica Simpson arrived for a family photo shoot in an over-sized turtle neck sweater, tiny shorts and towering heels.
Hollywood, Ca., April 26, 2011
Jessica Simpson made a return to the red carpet at the Us Weekly Hot Hollywood Party in printed Etro minidress and Charlotte Olympia pumps.
Miami, Fl., Dec. 11, 2010
Kim Kardashian's red corset cinched-waist dress at the Y100 Jingle Ball recalls her Superwoman costume from Halloween 2008. The reality star paired the look with a simple open-toe black platform pump.
Beverly Hills, Ca., Dec. 14, 2010
Gwyneth Paltrow's Pucci gown was a bold fashion choice for the "Country Strong" star. The actress kept accessories to a minimum -- adding only strappy sandals and Sutra ring.
New York City, Nov. 29, 2010
Leighton Meester wore a Thom Browne womenswear suit (the first ever!) to the Gotham Independent Film Awards. She paired the suit with Salvatore Ferragamo pumps and Bulgari jewelry.
New York City, Nov. 16, 2010
Leighton Meester was daring in a black lace jumpsuit by Marchesa at the launch of the Court of Jewels recreation at Harry Winston.
Beverly Hills, Nov. 3, 2010
Wearing a white dress paired with a puffy-shouldered, blue-and-white jacket, Joan Collins channels her "Dynasty" days as she steps out for dinner at Mr. Chow in Beverly Hills.
Los Angeles, November 1, 2010
Wearing a black lace Marchesa dress with sexy cut-outs, Kelly Osbourne channeled her inner dancer at the celebration of "Dancing with the Stars" 200th episode.
London, England, October 25, 2010
Julianne Moore wore an asymmetrical -- and some would say too funky -- Lanvin dress paired with a Bulgari clutch and heels at the London premiere of "The Kids Are Alright."
Today's edition of when bad clothes happen to good people: Brooke Shields. The model-turned-actress stepped out to New York City Ballet's 2011 spring gala on Wednesday night wearing a one-shouldered black dress and strappy high heels. So far, not so bad...although I might have picked a pair of pumps instead.
The real style distraction came in the form of her neck gear: a frilly and feathered flower with what look like buttons on it affixed to a silver, aluminum foil-like chain. We can't tell if it's part of the frock or if it could have fallen under the "take one thing off before you leave the house" category, but, in any case, it looks like her necklace ate her left sleeve. Which is never a good thing.
Of course, this is just one human's opinion. Take a look and tell us what you think.