I kind of think, against a lot of better judgement, that she is pulling this off. I also constantly think, when watching Big Brother, that Elissa sort of resembles Shailene, except Shailene looks really natural and Elissa does not.
I WAS concerned that the bottom of this look was harem pants. THAT would have been a step too far.
This, I'm less enamored of. Something about the boxy cut almost makes her look like she's wearing two giant envelopes. And this is where I would make a super hacky "the envelope, please" joke if I didn't already feel that you'd been through enough.