That's a question that has changed drastically in our time. It is a 'loaded' question. The expected answer is a positive one complimenting a person's style choice. It is particularly targeted to women and became a popular television series built around the style-impaired in need of a makeover, according to two of the victim's friends. The fashion victim's two friends turn her/him in and they all get to pick out a clothing collection she/he likes best.
Every culture and every age has had its standards of beauty. However in this age, that standard has changed towards the comfortable and casual. So while I may lament the sloppy way of dressing in North America, it is here to stay - it is now considered middle class normal.
This from Deirdre Clemente of Zocalo Public Square:
"I study one of the most profound cultural changes of the 20th century: the rise of casual dress. I study casual dress as it evolved on the beaches of Miami. I study casual dress as worn by the Black Panthers and by Princeton undergraduates. As a professor, I teach seminars on material culture and direct graduate students as they research and curate costume exhibitions, but my bread-and-butter as a scholar is the “why” and “when” our sartorial standards went from collared to comfortable. "
Find the article in Time magazine HERE. She says that casual clothes are "the uniform of the American middle class and that everyone in America considers themselves middle class."
I think the emphasis is on comfortable - here's a visual summary of the king of comfort style:
Our pictures today show a previous convention contest winner - A Maine Lobster Wharf by Don Railton.