One of the comments about this dress was that it looked "slovenly." Again I think we have to remember that these are real people in real life situations. I think we should look at these photos in more of an inspirational and not so literal manner. I think it miss a lot if we just make each look a "Yes !" or "No ! ".
I think we also have to be more open-minded about the situations that these people may be wearing a particular look. Everyone I shoot is not just going to/from work or for an evening out on the town.
In this look ,for example, I see red bathing suit straps around her neck and she was near to and walking in the direction of Central Park. I think of this as a very chic way to use a dress as a cover-up for a girl on her way to a day of sun and fun in Central Park. On her way to the park she can pop into a few shops (dry cleaners, newstand, nail salon) and on her way back pick up some groceries all the while looking cute as can be. New Yorkers do a lot of multitasking, we don't usually have a car parked nearby to drop off or pickup the gear for our next task. I have seen the way most people dress for a day at the beach and by comparison this is a pretty good look.