[Proviso: this posting is mostly about cross-dressing, but it doesn’t pretend to be an essay on the very large number of forms and functions of cross-dressing, even in the modern U.S., much less in different sociocultural contexts around the world and throughout history.]
I’ve been accumulating comic strips having to do with boys and masculinity, in particular about what they’ve picked up about normatively masculine behavior and attitudes by the age of 8 or so: the age of the character Joe in the comic strip One Big Happy, who’s the older brother of Ruthie, age 6, who’s the central character of the strip. At the moment I have 5 strips (4 OBHs, plus a Zippy), covering a wide range of themes in normative masculinity for boys. To judge from the comics (and my recollections of boyhood), an 8-year-old has an extensive and pretty fine-grained command of the cultural norms of masculinity within his social group.
Example 1, the OBH of 4/16/21, on attitudes towards transvestism / cross-dressing:

(#1) The attitude here is that male cross-dressing — prancing around dressed in women’s clothing — is ridiculous, maybe pitiful, but in any case not compatible with ferocity, that is, symbolic masculinity ; this is one step in sophistication past the attitude that it’s against nature, therefore pathological and dangerous, though possibly usable as entertainment, in the theatre of ridicule
Two linguistic side issues here: the idiomatic slang says you, expressing disagreement with an interlocutor’s remark (from Joe, to Ruthie, in the last panel); and the 2pbfV cross-dress (a derivative of the synthetic compound cross-dressing). Before that, the background of the Boy Code.
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