Someone kind figured out the odds on this thread at some point, and yes, the chances suck.
Fortunately, that's just an early game problem. Once Cassy teaches you misdirection, it becomes very easy to strip people as long as you're still wearing clothing items. And then much later, when you get enough free ninjutsu lessons from Yui, you automatically equip items you strip, so it's broken af.
Honestly though, zip ties are your best friend early game. Sure, Jewel busts through them pretty easily, but it's only like 5 bucks a zip tie, and you automatically succeed at stripping people when they're bound.