In the 1920s bobs were a statement of independence and modernity. But even something that’s considered forward in its time needs to change for sake of getting left behind. To modernize your modern bob, play with longer lengths and go for a severe blunt cut.
Un’ruly tip: If you have an old long-haired wig lying around and want to get more miles out of it, give it cut and create a look similar to the above. Usually the ends of a wig are what go first, so chopping them off will do you some good.