Outfit tracking

My problem is two-fold. I know that I've had an inventory/outfit tracked item successfully actually change the worn true/false before when the player dresses or undresses or changes clothing, but I just cannot get it to work anymore, I'm kind of at my wits end.

Also, I have a player character who has a quirk that they can't wear underwear (all 18+, played for laughs) UNLESS they're wearing boxers or trunks and nothing else. However, I've done my best to get it working, and it just doesn't seem to.