I think the boot tuck stands a better chance of working so long as you only ever approach people head-on -- the boot-tuck profile can look pretty ungainly!
In general, especially now that the look is "on-trend," it can read the way it would if, I dunno, a guy had on a nice watch and tucked his sleeve into it, so people !!NOTICED HIS REALLY NICE WATCH!!
I know it sucks to have really nice boots and people can't see how nice they are 'cause your pants are over them, but it's far subtler/flyer when you see someone cross his legs or something, revealing a flash of unseen detail on the upper of his boots, rather than billboarding them.
As far as high-top sneaks, think it's a look that works best if you are a member of Cool Kids, and otherwise risks a certain forced, ARE Weapons-esque choadliness.