Worst Dressed Celebrities

by SheKnows
Jul 28, 2010 at 6:51 p.m. ET
Amy Winehouse needs to go to fashion rehab for this outfit choice.

1 /10: Worst Dressed: Anna Wintour

1/10 :Worst Dressed: Anna Wintour

You'd think the mega style maven Anna Wintour, editor in chief of American Vogue, would know enough to avoid clam shells as shoulder pads.

2 /10: Worst Dressed: Britney Spears

2/10 :Worst Dressed: Britney Spears

Oops, she did it again! Britney Spears stepped out without a bra. We're starting to wonder if she even owns one.

3 /10: Worst Dressed: Jennifer Lopez

3/10 :Worst Dressed: Jennifer Lopez

Wowza! The curvaceous mama made no bones about her fuller figure when she donned this skin tight yet majorly poofed out number at the Oscars.

4 /10: Worst Dressed: Lady Gaga

4/10 :Worst Dressed: Lady Gaga

Someone call 911! Lady Gaga has been attacked by a Kermit the Frog parasite!

5 /10: Worst Dressed: Lady Gaga again!

5/10 :Worst Dressed: Lady Gaga again!

We couldn't help ourselves . . . Lady Gaga's underwear as outerwear deserved a second spot on the worst dressed celebrities list.

6 /10: Worst Dressed: Lindsay Lohan

6/10 :Worst Dressed: Lindsay Lohan

At least Lindsay is trying to make a match: her overdone spray tan goes nicely with the orange hue of her jail jumpsuit.

7 /10: Worst Dressed: Mary Kate Olsen

7/10 :Worst Dressed: Mary Kate Olsen

It's always hit or miss with Mary Kate Olsen's fashion choices. This time around, the six-sizes-too-large muumuu is a definite miss.

8 /10: Worst Dressed: Mickey Rourke

8/10 :Worst Dressed: Mickey Rourke

Mickey Rourke, where do we begin? The overall look - including token dog - is a major fashion don't.

9 /10: Worst Dressed: Bai Ling

9/10 :Worst Dressed: Bai Ling

There aren't enough worst dressed lists in the world for Bai Ling, but here's a particularly offending floral and neon outfit choice.

10 /10: Worst Dressed: Russell Brand

10/10 :Worst Dressed: Russell Brand

Technically this is more of a worst rat's nest hair ever, but we're gonna let Russell Brand slide onto the worst dressed celebrities list anyway.