She always seems to be a trend follower rather than a trend setter. Even though I don't really like Lindsay Hohan, it was her that kind of started the black leggings trend (along with Nicole Richie) and now Hilary is doing it.
Also Nicole Richie started the Christian Loboutin pumps trend and then everyone followed and of course Hilary was there to copy (the yellow Loboutins).
I think she should be more original, like when she wore Stella McCartney at her 18th or that black feather dress at the AMA's.