I don't even know where to start.
Putting kids in drag looks like a deliberate attempt to sexualise children and in turn discredit gay men to me.
Annie Lennox didn't look extremely androgynous in trousers, no more so than any other woman in trousers and not enough to be a drag king. She just doesn't look like a hypersexualised barbie doll. What does this have to do with the sexualisation of children?
''(heals were worn by men to ensure grip while riding horses)''
The heel of a riding boot is 1 - 1'5", so not that high, nothing like a high heel shoe or boot. Flat shoes are more likely to slip through the stirrup which is dangerous, if you fall off you will be dragged to your death unless your foot slips out of your boot. So you wear a slight heel. Like a cowboy boot.
High heels and make up are like all other signs of status; impractical, and to demonstrate you don't do manual labour.