Oh goodness, pickpocketing is very tough sometimes. But you can get alot of really good items. Does your main character have the Dexterity talent? I've heard that that helps greatly to increase the success of pickpocketing.

Now...if I remember correctly, there are two items that help your stealing rate increase. The Bandit's Glove (which I think is required for stealing) and the Magician's Hand which is gotten much later in the story. I'm not completely sure, but check A l e x's dazzling faq on Gamefaqs to make sure.

Some things to look out for:

-Battle Suits. From Ernest in Private Actions (means you can't get Ashton and must get Opera), and from an ensign on the Calnus during Eluria Tower (in Claude's story).

-Bunny Shoes. From the Bunny mascot in Fun City, I think.

-SANTA BOOTS!! After you can go back to Expel with 'virtual reality' (*snicker*), pickpocket the kid in the newlywed's house (looks like they had a kid). This may take many tries, but I did it in a few tries.

That's all I can think of for now.