14 Celebrity Halloween Costume Fails

Oct 23 2014 - 3:08am

You'd think that celebrities — aka people with access to stylists and makeup artists — would have the best Halloween [1] costumes ever, but alas, not all stars are sexy and flawless on the spookiest day of the year [2]. As we've seen time after time, somebody is bound to make a mistake when Oct. 31 rolls around. Sometimes it's completely understandable (like when it's clear someone just grabbed random items in a rush and threw it all together out of desperation), and then there are the downright offensive costumes that leave everyone scratching their heads, asking, "What were they thinking?" Regardless, it either teaches us what not to do or gives us a good laugh. Scroll through to see the stars who have failed at Halloween, then find inspiration in over 150 celebrity costumes [3]!

Kim Kardashian (2010)

Little Red Riding Hood was a little girl. An innocent little girl.

Jessica Simpson and Nick Lachey (2004)

Three's Company isn't the most obvious inspiration for a couple's costume because, well, don't you need three people?

Anne Hathaway (2010)

Anne, you're wearing a leopard-print muumuu and a purple mask that looks itchy. We're sorry, but this really doesn't look like a cat we've ever seen, and you should know — you played Catwoman!

Scott Disick (2012)

Here's a pro tip from Robin: use some padding around the bulge, Scott.

Deryck Whibley (2012)

Deryck and his then-girlfriend Ari Cooper captured the essence of Avril Lavigne [4] and her new man Chad Kroeger, but this probably isn't the best way to throw shade at your ex.

Al Roker (2004)

Al, if you're going to wear an Oprah costume, ask for her stellar fashion advice, or at least one of her favorite things!

Aaron Carter (2002)

Yep, Aaron — you were a convincing pimp when you were 14.

Kate Upton (2011)

Kate, you make such a gorgeous Marilyn Monroe; there's no need to get skeletons involved.

Heidi Klum (2006)

Something about a half-snake, half-apple holding a bag of M&M's takes a minute to process.

Lance Bass (2011)

We have so many questions, Lance. But first, is that a children's skirt . . . wrapped around your knee?

Angie Harmon (2002)

This is like Clueless meets Madonna [5] circa 1980s meets Britney Spears [6] when she went through that wig phase. Also, "boy beater"?

Josh Hartnett (2005)

Hold up — is that a costume or the result of a rough night?

Julianne Hough (2013)

Dressing up as Crazy Eyes and other Orange Is the New Black [7] inmates was all the rage last year. But wearing dark makeup? Not so cool. Julianne apologized for it [8].

Joey Fatone (2002)

We'll never look at Joey the same again.

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