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Photo 9/14
AnnaLynne McCord
We applaud this "90210" star for always changing up her hair, but this look was just a bit too voluminous and not quite right for her face shape. Wondering if a certain updo would look right on you? Consult this updo guide for your face shape.

Photo 10/14
Janet Jackson
Janet looks fierce with or without a Trojan horse-like hairstyle like the one in this photo. We'd rather see her wear an edgy hairstyle like this though.

Photo 11/14
Kim Cattrall
When you have a gorgeous face and body, channeling Marge Simpson isn't the best way to draw attention to those assets. Less is more when it comes to updos.

Photo 12/14
Denise Richards
This is prom hair on steroids. Denise should start copying Jennifer Aniston hairstyles for classic, never-miss looks.

Photo 13/14
Kelly Osbourne
When your hairstyle resembles abstract art like Kelly's did here, you should probably rethink the look. The most flattering updos are ones that have a softer, more romantic feel, like these.

Most celebrity hairstyles garner praise and admiration, but these horrible hairstyles left us scratching our heads. Why on earth would any A-list celebrity take such a crazy risk by sporting one of these over-the-top styles? Probably because they wanted to stand out in the crowd, right? Well, we guess it worked -- just not in a good way!
BY KRISTEN OLDHAM GIORDANI | SHARES
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