Oh, I don't think the woman looks bad at all. Her style is a style. Distinctive, recognizable. I believe it was put together in support of a set of values, interests, needs, and social relationships. My money is on the notion that she got dressed according to rules and principles.
I find the flat question very interesting -- as to whether or not the average person would see a difference between the various types of baggy pants out there. My guess-timate is that most people have a sense of the difference, but are not able to identify what exactly is responsible for it. I think most would miss details with big impact. But of course there's a whole spectrum people fall across.
Anyways, I also feel that most people don't care that much, nor should they. It's not life or death. My family is really into it as a bunch of snickety architects and builders, but playing Uno will also pass the time for us.