Cupid wears a diaper primarily for modesty and to make costuming and depictions of him more socially acceptable.
While depictions of Cupid throughout history have varied, the diaper (or loincloth) is a common element. Here's a breakdown of the reasoning:
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Modesty: Cupid is often depicted as a cherubic infant or young child. Without some form of covering, the depictions would be considered inappropriate in many cultures. The diaper provides a degree of modesty.
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Social Acceptability: Depicting a nude child, even in a mythological context, can be controversial. The diaper ensures that Cupid's image remains widely acceptable in art, advertising, and popular culture.
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Cosplay and Practicality: As the reference points out, a diaper makes it much easier to cosplay as Cupid in public. It simplifies the costume and avoids any issues related to public nudity.
In summary, the diaper serves as a practical and socially acceptable way to portray Cupid, maintaining a balance between classical imagery and modern sensibilities.