Sinead managed to pull it off at a time when nobody was doing it, and she was a real oddity.
But she did have the advantage of being more of an artist, and having that whole mystical Irish image. And the media was much more fair to Sinead, at least before the whole Pope picture thing. When she first came on the scene, journalists wanted to understand it and explain her shaved head. Today, and especially with Britney, the prevailing brand of journalism is not to understand and explain, but to interpret in the most provocative way and support with any source who'll go on the record.
One thing Sinead and Britney do have in common: in the late 80s/early 90s, every woman with a shaved head "looked just like Sinead" even if there was no resemblance other than gender and lack of hair.
That's probably the most frustrating thing for an acomophile. People who aren't into it don't really even look closely or give much thought to a bald woman when they see one. There's either a knee-jerk "yuck" response, the "not everybody could pull that off" response (if they like it but don't want to admit it looks good), or a superficial comparison to some bald celebrity, which is like saying "they all look alike."
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