This photo may have converted me to, or at least has me reconsidering, the boyfriend jean. I love the heels, the well-tailored blazer, the way the jeans are slightly fitted at the thigh but straight towards the calf, and the pop of color provided by the bag. She does proportions very well, which keeps the pants from looking sloppy.
When this trend first emerged on the scene I was utterly opposed. Something about the peg-leg example found on Katie Holmes instantly turned me off. I think she wears the pants too loose, which results in a balloon-like form, and that the roll of the pants hits at an awkward point that is too low and unflattering. Additionally, pairing the jeans with flats, even though she has long legs, makes them look bizarrely stumpy.
I am still debating whether or not this is a look I can attempt. I top out at almost 5' 4" (if I stand very tall) and if Rachel Bilson can't rock this look without looking schlumpy, then I probably can't either. But, I see now that the boyfriend jean can be done well, which restores my faith in humanity a little bit :)
Photo Credit: The Sartorialist