I agree that the hobo is a classic style, although it should be clarified that "classic" does not necessarily mean "tasteful" or "elegant" despite the fact that those words are often used almost as synonyms.
The traditional hobo bag has that soft rounded crescent shape that resembles the bag on a stick that "hobos" were supposed to carry, but I see some very square bags being called hobos that don't really fit the traditional description. Perhaps this variation of what is traditionally called a hobo bag is what is trendy.
While the overall silhouette is classic one, almost every new interpretation will end up looking dated. I don't think this is exclusive to the hobo style though. Every basic bag shape gets modernized and reinterpreted each season to suit the overall fashion aesthetic.
The traditional hobo bag has that soft rounded crescent shape that resembles the bag on a stick that "hobos" were supposed to carry, but I see some very square bags being called hobos that don't really fit the traditional description. Perhaps this variation of what is traditionally called a hobo bag is what is trendy.
While the overall silhouette is classic one, almost every new interpretation will end up looking dated. I don't think this is exclusive to the hobo style though. Every basic bag shape gets modernized and reinterpreted each season to suit the overall fashion aesthetic.
