Do pickpocketed items respawn?

I've been playing Skyrim almost 6 months now, haven't done a lot of pickpocketing yet, despite the Thieves' Guild being one of my favorite aspects of the game. With my current character I'm starting to do a lot of it. For instance I just pickpocketed almost everyone in Riften in a single in-game night (I'm expecting an army of hired thugs to come after me any day now lol).

Question I want to ask is, do NPC characters' goods replenish over time? I know that items in barrels and such will respawn, but do items on characters' persons also respawn, including valuable items? I robbed the rings and necklaces and generally anything valuable off of almost everyone in Riften; will they gain new items like that after a certain amount of time passes, or will they never have such valuables again once I've robbed them?

In view of Skyrim's limited population of one or two dozen people per city, pickpocketing will soon become boring and pointless if, after I've pickpocketed most of the game's characters, nobody ever regains any valuables worth robbing apart from the random ones generated by Fishing Job quests given by Delvin.

I'm not sure if NPCs get new items when the town "resets" after several in game weeks. I only ever really took up pickpocketing so I could unlock the perfect touch perk and see certain NPCs naked. Once I achieved that perk, I pretty much stopped doing it, except for when I wanted to steal back the money i paid a trainer for lessons.

And now that I've finally figured out how to use the fortify restoration exploit to get certain followers to wear skimpy fur armour, I likely won't be using the pickpocket skill ever again.

But the skill is handy for the extra pockets perk (you can never have too much inventory space in Skyrim) and getting hold of useful enchanted items early. And you might appreciate the poisoner perk if you're playing an assassin. If you're really good, you can have fun stealing weapons and armour from bandits before they notice you and they will have to run around looking for something to hit you with.