In order to look special wearing the chancy unique; it must be worn with your persona, and if the two don't blend, then the look becomes pear-shaped.
It would be my guess that Madonna is not a very happy woman. From my own experience, having gone through persona changes like that, that kind of clawing need to be the center of attention is not a pleasant place to be.
[David] Bowie had a genius for continual change himself, reinventing his sound and his image throughout the decades. Each album seemed to find Bowie in a different persona, with a new sound to match his new look.
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