Eugene Volokh (5/28, 10:05 AM) and others have been blogging about the Muslim woman in Florida who wants to keep her driver's license, but doesn't want to have her picture taken with more than her eyes showing. Volokh adduces a relevant legal decision from the 1980s. There may be more such cases further back.

It's been more than thirty years, and I don't recall whether I read this or heard about it in Catholic school -- most likely the latter --, but I believe there were similar problems when nuns started applying for driver's licenses. I imagine they were slower to take up driving than most professions, but by the '40s or '50s at the latest cars had become necessary to much of the work nuns do. Of course, up until the '60s, nuns covered their hair entirely, and some wore quite astonishly complex headdresses. The problem with getting driver's licenses was not so much identification, though listing hair color on a license doesn't help much when the hair is never shown in public. The problem was peripheral vision: some of the more elaborate headdresses left only a very narrow field of vision, much too narrow for safe driving. I don't know whether there were lawsuits or the issue was handled administratively, but as I recall the story, some orders of nuns were forced to modify their habits, or agree to remove parts of them while driving, before they were allowed to get licenses.

Perhaps someone with access to legal databases could do a search on 'nun + license + habit' or something like that? Or perhaps someone at the old nuns' home would remember how the issue was handled, since it may not have gone to court.