Ok I swear I know how Chicago screws work 
But I’m trying to remove the covered buttons (you know, not conchos but the suede buttons) from my chaps to adjust the waist and I absolutely cannot get the button off!!
I’m turning the screw lefty loosey while holding the button in place. The screw turns, but nothing loosens. Both buttons are doing this so I feel like maybe I’m doing something wrong?
Are you sure they’re Chicago screws and not rivets?
Yes – they have a slot for a flat head screwdriver and the product description on HobbyHorse says Chicago screws.
So probably the back of the Chicago screw (female threaded part) is not firmly attached to the button so holding the button is not keeping the back from moving. You may need to clamp it somehow. Not sure how to do that without seeing it (and maybe not then). Good luck.
Ugh yes that’s what I suspect too. They’re too tight to be able to get a good look at what’s happening, the suede is kind of compacted around there.
Yeah, if they’re Hobby Horse chaps and you’re sure they’re Chicago screws, I agree that the other end is just twirling around, unseen, beneath the suede button cover. This may be a two person job where someone else is viciously clamping onto the button end with some pliers-- they need to truly feel the edge of the screw through the suede to hold it still-- while you turn the other end.
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