Uhmmm not if they're older than like 3, cause after that wearing them is just creepy.
Well they can and I'm not talking about gay boys, most crossdressers are indeed straight men. Outside utter crossdressing well stilettos may look a bit too much but some boys can definitely pull off some kinds of high wedge sandals, it may look cool in an unconventional way but you must be careful, you may not want to wear shorts in this case or you'd have to shave, but this isn't also strict rule.
As for other usual female shoes, well some boys especially in the emo style wear flats, sometimes even leggings, but they like to highlight their androginous side, not that they can't be "badass" or otherwise masculine, but you may want to avoid flats if you don't want to look the least androginous.
But as female can look ironically feminine with a tie so can us, today we have much more leeway. And take loafers for example, they are the unisex shoe by excellence, now even medium to low vamp loafers fall into women shoes, so I wouldn't even call crossdressing if a boy wears one.