There's a fine line between High Fashion and Total Disaster

One of the many things you learn by keeping a close eye on fashion is that there is a fine line between high fashion and a total disaster. Some say less is more and other say that the more the merrier.

A part of deciding whether it's in or out is who's wearing it. Would we have liked Miley Cyrus' VMA Dolce & Gabbana outfit a bit more if a recognized fashionista would have been wearing it?
Would we love it if Anna Dello Russo would have worn it to a large fashion event or would our reactions just have been the same?
And if we'd turn it around; would we not like some of Anna's most outrageous outfits if Miley would be wearing it?