Okay, I am admitting this with great reluctance, but … I really like Ashlee Simpson’s style. This is frustrating to me, because I’m not entirely sure what she does (the lip-synching snafu of a few years ago proves that she receives some, um, assistance), and she’s just a little too ooey-gooey with Pete Wentz. But I really have a thing for her look.

The stick-straight red hair is really appealing on her (far better than blonde or black), and I like that she has a bit of punk to her look but can pull off ultra-feminine ensembles as well.

This girl knows what looks good on her and she knows how to work it. Here she keeps it simple and edgy with skinny jeans and a loose v-neck tee, adding a bit of rocker glam with her lux leather bag and tough boots.

She looks equally comfortable ultra-femme in a 3.1 Phillip Lim dress, Chanel pearls and sky-high neutral heels.

And she can effortlessly fuse the two styles with skinny jeans, an Opening Ceremony coat and more pearls. This isn’t to say she doesn’t make the occasional faux-pas, but in the grand scheme of things, she’s hitting the right fashion notes!