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Well Played: Ashlee Simpson’s Trendy Tomboy Look

Ashlee's Accessories
We love her short hair and major earrings combo! Read More »
Lotta Look: Ashlee Simpson
So many patterns, so little outfit. Read More »
Well Played

She might be a millionaire and she might date famous dudes and she might have a super cute toddler with a trendy name, but life hasn’t exactly been easy for Ashlee Simpson. She grew up livin’ in the shadow of (someone else’s dreeeaaam) big sister Jessica, biffed her lip syncing gig on SNL, divorced her baby daddy Pete Wentz, and broke up with her most recent BF while dealing with her parents’ divorce, which was reportedly caused by her dad’s secret penchant for twenty-something male models. Phew, I’m out of breath just typing all that! So if it’s any consolation, I’d just like to say: Ashlee, I’m obsessed with your outfit. You look cute, comfy, and trendy. Also I’m listening to “Pieces of Me” while I write this and having intense flashbacks of my college dorm room, so thanks for that too. [Photo: Splash News]

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