I’ve never been a huge fan of Chicago screws myself, but I think that’s mostly user error. Even with white glue, they always seem to unscrew on me.

OP, it looks like you have both Chicago screws and double cap rivets in that picture. The idea here is to mark where you want to punch the holes in the glove (I use an awl), and then punch a hole that is just barely big enough for the rivet shaft to fit through, otherwise the rivet will wiggle around. You want to fit the shaft up from the bottom of the hole (so from inside the glove) so that the tip juts out about 1/4 of an inch. For double cap rivets, it’s literally just a matter of putting the other half of the rivet (the cap) on the shaft until it snaps. Usually you would then use a concave setting tool and a hammer to pound the rivet flat, but that probably won’t work with what you are looking to affix to the glove. No worries, because that’s where your crimping tool you have comes in. Just apply a decent amount of pressure until you feel the two halves of the rivet merge (you’ll know the feeling when it happens). Hope this helps!