She looks about 60 in those pictures you've posted but I've just googled her and she looks fabulous in others. I love her style though and agree with mousemary that you need a combination of beauty, androgeny and thinness to pull it off properly.
I agree that Olivia Palermo is fabulously stylish but again, she's small, thin and beautiful. Being rich helps too. Oh - and young!
I suit a more polished, sleek look myself but I do admire people who look great in scruffy, mismatched, loose things.