10. Maria Sharapova
Everyone wants the super-hot tennis starlet modeling their clothes and advertising their product -- so much so that Maria was the highest-paid female athlete in the world last year. So...why can't she buy a decent outfit?
Andrew H. Walker, Getty Images
9. Paris Hilton
Paris is perfectly capable of looking cute -- so it's shameful that she spends so much time dressed like a tacky transvestite...or a disco ball.
Dave M. Benett, Getty Images
8. Miley Cyrus
Note to teenage girls everywhere: You do not look older when you cake on foundation overdo the blue eyeshadow -- you look like a teenager wearing too much makeup. So Miley, quit wasting time texting naughty photos to your indiscreet boy toys, and spend that time paying attention to your stylist.
Gregg DeGuire, WireImage
7. Mariah Carey
Admittedly this outfit was cool -- when Mariah was 28...10 years ago. But no matter how amazing her body looks, at nearly 40-years-old the Queen of Pop needs to stop dressing like a tween.
Theo Wargo, WireImage
6. Heidi Montag
Speidi's less-attractive half makes the list partly because she dresses like a garish fashion goblin, but also because she's obnoxious.
Michael Tran, FilmMagic
5. Aubrey O'Day
Now that Aubrey's been ousted from Danity Kane, maybe we'll see less of her bra-less, thrift-store foul-ups on the red carpet. Because seriously, is that a table cloth wrapped around her waste? And we can see your nipples!
Mark Von Holden, WireImage
4. Mischa Barton
Remember when Mischa was an OC superstar and an up-and-coming fashion designer? We loved her then, too! But it's been a sad, sad fall from grace for the former Hollywood hottie. Oh, Mischa. No one likes this faux-hippie, woodland fairy look you've been forcing on us the past twelve months. Please let it go.
Tim Whitby, Getty Images
3. Paula Abdul
Like so many of the stars on this year's list, it's not just that they've been dressing like weirdos (or, Paula's case, like 19th-century English brigadier generals), but that they should know better! We're not talking about Tila Tequila-style MySpace celebrities -- these are bona fide A-listers with millions of dollars to spend on make-up artists, stylists, and fancy designer threads. So how can they leave the house like this?
Ray Tamarra, Getty Images
2. Solange Knowles
Less famous, less talented, and starved for attention. Ah, yes. The classic little sister syndrome strikes again -- and if Solange's freakish fashion forays are any indication, she's getting desperate for Beyonce-style stardom.
Michael Loccisano, FilmMagic
1. Madonna
Madge's unfortunate attempts to reclaim her fashion bravado often left us stunned -- but not in a good way. Maybe the Material Girl wanted to prove she wasn't Earth Mama Jolie just because she likes adopting foreign children, or that she's not really the boring English housewife Guy Ritchie made her out to be -- but regardless, Madonna spent 2008 trying way too hard, and wound up looking insincere, out of touch, or just absurd.
Theo Wargo, WireImage
You might recall that, back in 2006, JCPenney was in some hot water with animal activists after some of their clothing labeled as having raccoon fur actually had fur from raccoon dogs, a species of dog in China. Well, the department store has been working hard to make up for its furry gaffe and 
At 
Designers, I'm worried. You only have until 5pm tomorrow to enter the 
There's me, tellin' Tim Gunn all my problems. It could be you!
Tim Gunn is hosting a fashion show called Fashion Forward to benefit the Gay Men's Health Crisis (GMHC). Could he get any lovelier? We love you, Tim Gunn.
