Let's look at dear old Blair Waldorf/Leighton Meester. I think she is struggling to find her personal style niche and tries way too hard, in general. This dress is no different. It doesn't really suit her and doesn't really make her look pretty. She looks fine, of course, she is a lovely looking girl. But does she look beautiful or amazing or mesmerizing? No. So where would that leave us if neither her nor Kate can make these rather rigid (breastplates anyone?) and conflicted dresses work?
I think the first requirement is much softer leather. The second is bags of attitude and the personality that resonates with rock 'n roll and rebellion. And the third is a flair for accessorising. Something like a bit of a lilac bootie to lift and edge the whole thing. Then maybe it will work. I think that Vampire Diaries Kat Graham is getting there with this frock she wore on the weekend. Almost. Lose the neckpiece and you're there. Good luck to you all.