Ashley Olsen's Best Hairstyles Ever

This mini mogul has gone from sitcom toddler to teen queen to trendsetting fashion designer, never missing a style beat along the way. We love Ashley for her ability to be cutting edge and classic all at once. Check out her best looks and then see if you can pull them off with our virtual hair makeover tool!

By Megan Cahn

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ashley olsen with perfect wavy hair
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Perfect Waves

Ashley gets it just right with these to-die-for curls and neutral makeup at the MANGO NYC Flagship Store opening in 2008.
ashley olsen with white blonde hair
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White Hot

Ashley looks sweet as can be with peach lips and extra-light blonde locks framing her face at the Miss Davenporte Trunk Show in 2005.
ashley olsen with long layered hair
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Long Layers

Ashley looks lovely with long, straight hair with two-toned blonde highlights at a book signing for Influence in 2008.
ashley olsen with blonde curls and pink lips
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Fat Spirals

Ashley stuns with perfect pink lips and big blonde curls at an amfAR gala in 2005.
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Chocolate Hue

Ashley ditches her blonde locks for a dark brown 'do that makes her green eyes pop at the CFDA Fashion Fund Awards in 2006.
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Major Volume

Ashley goes big with voluminous curls and extreme smoky eyes at the launch of her and her sister's new apparel line in 2006.
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Sophisticated Chic

Ashley rocks one of her signature looks: the middle part and sleek low pony at the CFDA Fashion Fund Awards in 2008.
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Bold Lips

Ashley is a standout with a perfect red pout and bronzed skin at the Metropolitan Museum of Art Costume Institute Gala in 2006.
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Long Bob

Ashley is smiling pretty with her new asymmetrical style at the premiere of The Hangover in 2009.
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Curled Updo

Ashley pairs her pulled-back dirty blonde curls with bronzed cheeks and thick eyeliner at the ACE Awards in 2005.
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