And you know what I noticed? She looks almost exactly the same as on her Time cover in November 2008:
And very close variations on this look show up on all those file photos in between. It's a signature look, to be sure, but a rather severe one. She has a tough job and a polarizing persona that has nothing to do with how she looks. But if she's ever in the mood to take a more compromising stance, she's going to need to soften it up a bit. Even a switch over to a medium gray (a color that looks good on almost everyone) would be a start. The lipstick should really change in any case - a more sheer formulation in a classic red would do the trick, like Make Up For Ever in True Red 415.