For me, Drake, through Ye's 808s, made that melodic sing rapping very popular. JiDenna seems to taking a cue from that tree but putting a lil more funk in it. Again this just one song though
The gender bending imo is more about not being overly obsessed with hyper masculinity and looking tough and being cool with spending time on appearance. He also dropped a slick little line in the song about the women on his arm aren't show pieces but their own generals.
Gender bending, theoretically, isn't about always taking popular gender norms and twisting them to the opposite binary, but playing with it in small doses as well. I mean he rocking eyeliner in the vid from the looks of it.