Bcuz guys being girly is like a microcosm of gender stuff, like drag queens and femboys and the like. Any sort of crossdressing can count as a form of gender expression even if someone doesn't deem certain clothing as only for certain genders.
Plus i think in terms of fictional characters a lot of these sorta drag escapades lead to ppl headcanoning that character being genderfluid or non-binary or even trans which i always love to do. It's just fun playing w headcanons like that.
Like the main ones coming to mind for me rn for some reason are Marco from SVTFOE and Moxxie from Helluva Boss but in terms of WOY, i definitely see Wander as genderfluid and i think it'd be cute if Peepers was too nwn.
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I get it lol