Maggie Gyllenhaal's Best Hairstyles Ever

This indie actress turned major movie star is not afraid to stand out, whether she's walking the red carpet or the streets of New York with her young daughter in tow. Here are Maggie's most beautiful moments — flip through them and then see how they work on you using our Virtual Hair Makeover tool!

By Megan Cahn

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maggie gyllenhaal with a bob and bright lipstick
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Pinned Bob

Maggie's unique hairstyle gives her a retro yet modern look at the Nanny McPhee and the Big Bang premiere in 2010.
maggie gyllenhaal with brunette curls
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Light Curls

Maggie pairs a rose-colored lip and soft brunette waves with natural highlights at a BOSS fashion show in 2007.
maggie gyllenhaal with an wavy updo
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Finger Wave

Maggie stands out with hot-pink lips and an original updo at a SAKS Fifth Avenue event in 2005.
maggie gyllenhaal with straight brunette hair
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Soft and Straight

Maggie goes for a simple look with long brunette hair, piece-y bangs, and rosy cheeks at the NYC Chopard Boutique opening in 2007.
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Doll Face

Cherry-red lips, short curlicues, and apple cheeks give Maggie a girlish glow at the CDFA awards in 2008.
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Flower Power

Maggie looks sweet with big baby blues, pink lipstick, and a lily behind her ear at the NYC Secretary premiere in 2002.
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Voluminous Updo

Maggie is gorgeous with a bouffant hairstye, defined cheekbones, and bright lips at the Golden Globe Awards in 2009.
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Ballerina Bun

Maggie is the picture of grace with this classic style at the L.A. premiere of Crazy Heart in 2009.
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Braided Headband

A pregnant Maggie glows with rosy cheeks and a pretty plaited hairstyle at the NYC premiere of World Trade Center in 2006.
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Dramatic Crop

Heavy black eyeliner and extreme short hair paired with light pink lips give Maggie a soft edginess at the L.A. premiere of Criminal in 2004.
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