The Best and Worst Celebrity Halloween Costumes

By Ashlee Davis

June 1, 2009 10:54 AM
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celebrity halloween costumes
John Sciulli
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Celebs Play Dress Up

Two costumes in one! Heidi Klum looks positively tempting as the serpent and apple!
celebrity halloween costumes
James Devaney
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Celebs Play Dress Up

We have to hand it to Katie Couric. We don’t know if it’s the toupee or the smug expression, but she makes a great Donald Trump.
celebrity halloween costumes
Dimitrios Kambouris
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Celebs Play Dress Up

There are few words that come to mind when thinking of Jason Biggs as Dorothy from the Wizard of Oz. We’re a fan of the red sneakers, but not much else.
celebrity halloween costumes
Jesse Grant
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Celebs Play Dress Up

Reality television isn’t saving the world anytime soon, but we must say, Kim Kardashian does resemble most famous female super hero.
Gregg DeGuire
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Celebs Play Dress Up

Aaron Carter, what were you thinking? You may have dated Hilary Duff and Lindsay Lohan, but that doesn’t mean you should dress up like a teenage pimp.
Johnny Nunez
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Celebs Play Dress Up

Anne Hathaway looks exquisite as an elegant Egyptian goddess. And we’re lovin’ the headdress!
Dimitrios Kambouris
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Celebs Play Dress Up

We just don’t get this look. Is Angie Harmon trying to be a Scotsman, a punk rocker, or an abusive girlfriend?

Celebs Play Dress Up

Take it down a notch, Aubrey O'Day. Even the hottest football players don’t wear metallic underwear.

Celebs Play Dress Up

Mariah Carey shows some skin in her rendition of The Little Mermaid. Hey, if you've got it, flaunt it!
Dimitrios Kambouris
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Celebs Play Dress Up

As the Hindu goddess Kali, we applaud Heidi Klum for her audacity and attention to detail.
M. Caulfield
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Celebs Play Dress Up

The Davis brothers may be oil heirs, but they look far from royal as Paris and Nicky Hilton.
John Shearer
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Celebs Play Dress Up

Ready to ruffle some feathers, Audrina Patridge pulls off the peacock look with style.
Ron Galella
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Celebs Play Dress Up

Cher + Cleopatra = One scary Halloween costume.

Celebs Play Dress Up

Hayley Keenan’s monarch butterfly costume is where homemade meets high fashion. So original!
Johnny Nunez
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Celebs Play Dress Up

Mariah Carey turns on the heat with her firefighter costume. But sex appeal aside, the bra-and-underwear Halloween approach is kind of a cop-out.

Celebs Play Dress Up

When it comes to Jamie Lee Curtis in leopard print, there is such a thing as too much material. But hey, she does resemble a life size jungle cat.
Dimitrios Kambouris
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Celebs Play Dress Up

Karolina Kurkova looks like she cat walked out of the ‘20s and onto the runway in her sultry flapper ensemble.
James Devaney
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Celebs Play Dress Up

Joey Fatone is confused, and so are we.

Celebs Play Dress Up

Only Heidi Klum would arrive at her Halloween party riding a horse. We're not sure about her costume, but those long locks go nicely with the mane.
Dimitrios Kambouris
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Celebs Play Dress Up

How old are you, Kelly Bensimon? You’re certainly in shape, but is your costume for Halloween or a jungle frat party?
Bennett Raglin
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Celebs Play Dress Up

Michelle Trachtenburg is a gorgeous Snow White, but we don't quite get Lydia Hearst's costume - a toga-wearing vampire with butterfly wings?
Ron Galella
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Celebs Play Dress Up

Martha Stewart lets down her hair and squeezes into a wet suit. Our only question is, did she do this willingly?
John Sciulli
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Celebs Play Dress Up

This is a great PG effort at Betty Boop, but if she was going for more coverage, maybe Mischa Barton shouldn't have picked the cartoon character used in 1920's eight-pagers.
Chris Weeks
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Celebs Play Dress Up

Only a few months after her time spent in prison, Paris Hilton shows her sense of humor on Halloween.
Dimitrios Kambouris
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Celebs Play Dress Up

Heidi Klum gives new meaning to the word vampire. If you choose a classic costume, might as well go all out!
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