Ashlee Simpson – Then
Unlike Jessica Simpson, Ashlee Simpson handled her divorce extremely well and looks amazing. As part of her transition from punk to goth, Ashlee rocked heavier eye makeup, more jewelry, and a more gothic aesthetic after she got married to Fall Out Boy bassist Pete Wentz in 2008.
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Two weeks after their wedding, the couple announced that Ashlee was pregnant with their first child. Their son was born in November 2008. It was only two years later, however, that the two split in February 2011.
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Ashlee Simpson – Now
From the looks of Ashlee, you would never guess she had ever been through a tough breakup! Her hair is now much lighter, her makeup is more natural, and she has an overall more sophisticated appearance.
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It has been a major transformation. It has taken her a long time to find happiness again, finally marrying Evan Ross in 2014. The couple have two children together, a daughter who was born in 2015 and a son in 2020.