Ashlee SimpsonWhat was she thinking? I get that Ashlee is going for that whole "I am unique and funky so I wear sneakers with dresses." Now I like converse sneakers as much as the next girl but the knee socks look is so over. The last time they were cool was in the movie Clueless and I hate to say it but that movie is like 12 years old. Also it spring, almost summer in fact. This is the time to wear bright colors and not striped gray cardigans. Also it looks like it night time Ash. No need for sunglasses. That bag also looks like a trash bag but it is the most popular bag in Hollywood right now so I guess it must be fashionable. Better luck next time Ashlee. At least her boobs aren't falling out of her dress like her big sis.