Great post, Caitlin. Did you ever track down the designer responsible for giving the female silhouette the chip on her shoulder?
You asked what other icons need a refresh. For me, the one which stands out — in business software, at least — is the Save button.
Even after a decade of physical obsolescence, the floppy disk lives on as the icon for the Save command.
The young digital natives of today have probably never seen a floppy disk in their lives, so I wonder what they make of that curious little icon.
With more and more work being done in the cloud, where your revisions tend to be saved automatically at regular intervals, perhaps the Save button will just die a quiet death and never need to be replaced.