Limit stripping to one item at a time

[Clarks]

An officer that wants to put a orange suit on you.. well.. he shouldn't have to keep you in stun lock to do it if you are cuffed so I don't see your point.

That's the point... when a terrible officer wants to fully strip you and dress you they already keep stunning until you're down the genpop chute.
Making the process slightly longer would not deter them, that sort of officer is already THAT bad.

And the better kind of officer doesn't need a disincentive to leave you most of your stuff, it already happens.