Bjork poses in her infamous swan dress at the 2001 Oscars. - Kevin Mazur/WireImage.com
Bjork: An Ugly Duckling
There's no excuse ... none ... zip ... ne ... nein ... mah nguh ... for wearing a swan dress. It's not eye-catching in a good way. It's not clever. It's not even ironic. And, frankly, it doesn't even look the least bit comfortable. So why did Bjork wear this atrocious dress to the 2001 Oscars? Maybe she had a singing telegram gig right after the ceremonies.
M.I.A.: Mommy, Oh Dear
Her baby must have been begging to stay put until its mother got some fashion sense, when M.I.A. wore this eye-and belly-popping number at the 2009 Grammys. Worse yet, she performed in the get-up ... in front of millions and millions of people. Just three days later she gave birth to her first child. Luckily for the future fashion world, it was a boy.
Rapper M.I.A. definitely didn't get her 2009 Grammy getup from a Pea in the Pod! - Steve Granitz/WireImage.com
Cher: Old Enough to Know Better
We're not saying we wouldn't love to have Cher's body when we're 63 years old. She looks amazing. But this outfit was tacky when she first wore a version of it in the 1989 video "If I Could Turn Back Time." Clearly, she can, and she did. But we didn't want to see it all then, and we sure don't want to see it all now.
Mary-Kate and Ashley Olsen: The Fur Twins
What's worse than a badly dressed bohemian twentysomething? TWIN badly dressed bohemian twentysomethings. Especially when they're into fur. The Olsens wore so much of it that in 2007 animal rights group PETA even created an online game called "Meet the Trollsen Twins." The object: to dress "Hairy-Kate and Trashley" in unspeakably un-animal-friendly clothes.
Mary-Kate and Ashely Olsen love their fur! - Jamie McCarthy/WireImage.com
Sinead O'Connor: Frump Rock
If Sinead was soupset with the Pope back in the '90s, why did she want to dress likehim? She should have taken it all the way and worn the pointy hat, too.It would have done her some good to cover that silly shaved head with alittle bit of flair.
Jennifer Lopez: Taking Fashion to New Lows
We getit: this was the greatest publicity stunt of all time. No one reallyknew who Jennifer Lopez was before she walked the 2000 Grammy carpet inthat belly-button (and practically everything else) baring greenVersace number. But we ask: after all these years, two husbands, and aset of twins, is this the outfit she really wants to be remembered for?
J.Lo made jaws drop when she donned this baring green Versace number on the 2000 Grammy red carpet. - Jeff Ves …
Rita Wilson: The She-Should-Be-Blushing Bride
They always tell you to choose your wedding dress carefully becausepeople are going to be looking at the photos for the rest of your life.Fortunately, Rita's taste hasn't improved all that much in the last fewdecades, so she probably still likes the mini-meringue dress she worewhen she walked down the aisle with Tom Hanks in 1988. We can onlyimagine what the cake looked like.
Jessica Simpson: Mom Jeans Mistake
Let's get thisstraight: Jessica Simpson is not fat, she never was fat, and she willprobably never be fat, especially after the Jeans Fiasco of '09.Jessica simply made a bad fashion choice: tight, high-waisted pants areclearly not her thing. The two words Jessica needed to hear weren't"lose weight." They should have been "low-rise."
Where was Jessica Simpson's stylist when she decided to wear these tight, high-waisted jeans? - Chris Gordon/W …
Joan Collins: Quarterback Chic
We know it was the signature look of the '80s, but, especially in retrospect, shoulder pads were just wrong. Add to that the head-diminishing "hat" (?) Joan's sporting in this photo, and the proportions are mind-boggling. At least it explains why big hair was so popular back then: it gave a girl a sense of balance. Aqua Net, we salute you.
Mariah Carey: Naughty Schoolmarm
When a woman isin her late, late, late 30s, she shouldn't be allowed to try to pulloff the sexy-schoolgirl look anymore. Not in public at least. ButMariah just can't stop herself. She's constantly wearing knee-highs andshort shorts or miniskirts -- always with heels, mind you. But when shewas asked to throw out the first pitch at last May's Yomiuri Giants andRakuten Golden Eagles game in Tokyo, did she have to make matters worseby adding the dated satin jacket? Nick Cannon must be really proud ofhis mother ... we mean, wife.
Now that Mariah Carey is 40, she needs to ditch the sexy schoolgirl look. - Jun Sato/WireImage.com
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