Oh Ashlee Simpson, how the pains of living in the shadow of your more famous and talented sister must create some serious insecurities. Luckily, you have a new baby and hubby to take your mind off of never living up to your full potential! Here Ashlee looks young hot and momalicious as ever in this Rain Denim Newsboy Cap ($15) while toting her new son Bronx Mowgli. Hey, at least this girl's personal life is intact, which is a whole lot more than we can say about her sis.
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