I don't know what they are thinking. Yes, anyone can be photoshopped and made look half decent and I'm sure Amy will look good or even great. BUT, everyone in the world knows she's not what the photo shoot will show. The one bright spot is that the photos were taken at the same time she was getting married in Miami and I seem to recall she was less drunk than normal that week. Right after the wedding she went back to being the cracked out alcoholic we've all grown to love, but right before the wedding she seemed ok.
I think this is Anna Wintour's way of showing she actually knows what's going on in the world. We already know she hates blogs, doesn't let people eat in the office, but she sure knows a 60's throwback with a beehive and missing teeth is the in thing right now and she's going to make sure that the world knows she knows it.
You know Amy probably didn't shower before the shoot so the clothes were probably not reusable, but unless the shoot consisted entirely of tank tops and shorts, I don't think Amy kept them.