could be that you just arent able to see the better items until you get a higher skill the items are always there just maybe in a harder pocket say the front one.....Say a guy is carrying an expensive ring in his front pocket and a few coins and cheap stuff in his back with low pick pocket maybe you dont get a chance to swipe the ring only the coins. :shrug:

This makes sense. It isn't that omg they suddenly magically have better stuff, it's that you can now pickpocket harder to loot places on them. I'd like to have a gag perk where you can steal equipped items. Then I can literally steal the pants off someone.