Kathryn Bigelow
It's not that she look BAD, but Bigelow just exudes this strange coolness that means I want her to show up everywhere with at least one piece of leather clothing, possibly also on the back of a giant motorbike, which she just parks wherever she pleases and nobody minds because she tips really well and lets them sit on it. This, with a leather jacket in place of the cardi? Cooler. This, with any other shoe besides those? Cooler.
Sally Field
Sure. Why not. I feel like I can see her slip, but at least Sally is being classy without being stodgy. It does sort of look like she's about to break into "We've Got Annie" while some racially questionable stereotypes masquerading as secondary characters toss her around a rich man's yard.
Helen Hunt
This is actually only neutrally played on her feet -- well, I suppose you could call that a neutral, but I don't. I call it grey, and I love grey, and I think Helen looks absolutely perfect in that. The only thing I'd want to swap out are the shoes -- a cute, unexpected color pairing would've been so nice. But I ALWAYS say that. I never realized I was so at war with tan shoes.